487:
1430:
1400:
471:
1448:
1415:
298:(resonance structure) with the greatest contribution is drawn. However, the skeletal formula is understood to represent the "real molecule" – that is, the weighted average of all contributing canonical forms. Thus, in cases where two or more canonical forms contribute with equal weight (e.g., in benzene, or a carboxylate anion) and one of the canonical forms is selected arbitrarily, the skeletal formula is understood to depict the true structure, containing equivalent bonds of fractional order, even though the delocalized bonds are depicted as nonequivalent single and double bonds.
1590:
1570:
1530:
1547:
1610:
1738:
597:
479:
1725:
384:
583:
429:
374:
356:
345:
590:
1669:
1472:
38:
1484:
1510:
bonds), in which all carbonâcarbon bonds are of equivalent length and have a bond order of exactly 1.5. For aryl rings in general, the two analogous canonical forms are almost always the primary contributors to the structure, but they are nonequivalent, so one structure may make a slightly greater contribution than the other, and bond orders may differ somewhat from 1.5.
1521:, used to be very common in introductory organic chemistry textbooks and is still frequently used in informal settings. However, because this depiction does not keep track of electron pairs and is unable to show the precise movement of electrons, it has largely been superseded by the Kekuléan depiction in pedagogical and formal academic contexts.
1855:
American and
European chemists use slightly different conventions for a hashed bond. Whereas most American chemists draw hashed bonds with short hash marks close to the stereocenter and long hash marks further away (in analogy to wedged bonds), most European chemists start with long hash marks close
327:
publications, for instance), these conventions have been nearly universal in the chemical literature since the late 1990s. A few minor conventional variations, especially with respect to the use of stereobonds, continue to exist as a result of differing US, UK and
European practice, or as a matter of
1845:
For instance, the acclaimed 1959 textbook by
Morrison and Boyd (6th edition, 1992) uses the Thiele notation as its standard depiction of the aryl ring, while the 2001 textbook by Clayden, Greeves, Warren, and Wothers (2nd edition, 2012) uses the Kekulé notation throughout and warns students to avoid
1720:
of alkenes. Wavy single bonds are the standard way to represent unknown or unspecified stereochemistry or a mixture of isomers (as with tetrahedral stereocenters). A crossed double-bond has been used sometimes; it is no longer considered an acceptable style for general use but may still be required
1373:
Two atoms can be bonded by sharing more than one pair of electrons. The common bonds to carbon are single, double and triple bonds. Single bonds are most common and are represented by a single, solid line between two atoms in a skeletal formula. Double bonds are denoted by two parallel lines, and
1509:
originally proposed in 1872. As mentioned above, the alternating single and double bonds of "1,3,5-cyclohexatriene" are understood to be a drawing of one of the two equivalent canonical forms of benzene (the one explicitly shown and the one with the opposite pattern of formal single and double
158:
Several other ways of depicting chemical structures are also commonly used in organic chemistry (though less frequently than skeletal formulae). For example, conformational structures look similar to skeletal formulae and are used to depict the approximate positions of atoms in 3D space, as a
171:, also look somewhat similar to skeletal formulae. However, there are slight differences in the conventions used, and the reader needs to be aware of them in order to understand the structural details encoded in the depiction. While skeletal and conformational structures are also used in
204:
bonded to its atoms. Hydrogen is the most common non-carbon atom that is bonded to carbon and, for simplicity, is not explicitly drawn. In addition, carbon atoms are not generally labelled as such directly (i.e. with "C"), whereas heteroatoms are always explicitly noted as such ("N" for
352:
If all four substituents to a tetrahedral carbon are explicitly shown, bonds to the two in-plane substituents still meet at 120°; the other two substituents, however, are usually shown with wedged and dashed bonds (to depict stereochemistry) and subtend a smaller angle of 60â90°.
271:, while a vertex labeled with a formal charge and/or nonbonding electron(s) is understood to have the number of hydrogen atoms required to give the carbon atom these indicated properties. Optionally, acetylenic and formyl hydrogens can be shown explicitly for the sake of clarity.
1860:
has suggested the use of a hashed bond with hash marks of equal length throughout as a compromise but now prefers the
American-style hashed bonds (Brecher, 2006, p. 1905). Some chemists use a thick bond and dotted bond (or hashed bond with equal length hashes) to depict
612:, but represent certain very common substituents or indicate an unspecified member of a group of elements. These are called pseudoelement symbols or organic elements and are treated like univalent "elements" in skeletal formulae. A list of common pseudoelement symbols:
328:
personal preference. As another minor variation between authors, formal charges can be shown with the plus or minus sign in a circle (â, â) or without the circle. The set of conventions that are followed by most authors is given below, along with illustrative examples.
192:
The skeletal structure of an organic compound is the series of atoms bonded together that form the essential structure of the compound. The skeleton can consist of chains, branches and/or rings of bonded atoms. Skeletal atoms other than carbon or hydrogen are called
494:
It does not matter which end of the chain one starts numbering from, as long as consistency is maintained when drawing diagrams. The condensed formula or the IUPAC name will confirm the orientation. Some molecules will become familiar regardless of the orientation.
1665:
chemistry is the use of a filled circle centered on a vertex (sometimes called H-dot/H-dash/H-circle, respectively) for an upward pointing hydrogen atom and two hash marks next to vertex or a hollow circle for a downward pointing hydrogen atom.
306:
Since skeletal structures were introduced in the latter half of the 19th century, their appearance has undergone considerable evolution. The graphical conventions in use today date to the 1980s. Thanks to the adoption of the
220:, as they give the molecule a function. Heteroatoms and functional groups are collectively called "substituents", as they are considered to be a substitute for the hydrogen atom that would be present in the parent
289:
carbons must be indicated explicitly while lone pairs in other cases are optional and are shown only for emphasis. In contrast, formal charges and unpaired electrons on main-group elements are always explicitly
333:
Bonds between sp or sp hybridized carbon or heteroatoms are conventionally represented using 120° angles whenever possible, with the longest chain of atoms following a zigzag pattern unless interrupted by a
1313:
or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction, facilitating multistep organic synthesis.
486:
216:
Heteroatoms and other groups of atoms that give rise to relatively high rates of chemical reactivity, or introduce specific and interesting characteristics in the spectra of compounds are called
1067:. However, since the anisyl group is monovalent, while the actinides are usually divalent, trivalent, or even higher valency, ambiguity rarely, if ever, arises in practice.
1781:
To prevent a 'kink' from emerging and causing a structure to take up too much vertical space on a page, the IUPAC (Brecher, 2008, p. 352) makes an exception for long chain
1772:
This term is ambiguous, because "Kekulé structure" also refers to Kekulé's famous proposal of a hexagon of alternating single and double bonds for the structure of benzene.
1609:
1836:
In this gallery, double bonds have been shown in red and triple bonds in blue. This was added for clarity â multiple bonds are not normally coloured in skeletal formulae.
470:
553:
OH, for instance, the hydrogen atom bonded to oxygen is denoted by the symbol H, whereas the hydrogen atoms which are bonded to carbon atoms are not shown directly.
267:
Hydrogen atoms attached to carbon are implied. An unlabeled vertex is understood to represent a carbon attached to the number of hydrogens required to satisfy the
969:. However, argon is inert under all usual conditions encountered in organic chemistry, so the use of Ar to represent an aryl substituent never causes confusion.)
274:
Hydrogen atoms attached to a heteroatom are shown explicitly. The heteroatom and hydrogen atoms attached thereto are usually shown as a single group (e.g., OH, NH
252:
Carbon atoms are represented by the vertices (intersections or termini) of line segments. For clarity, methyl groups are often explicitly written out as Me or CH
451:
appears to have only one bond, so there must also be three hydrogens bonded to it, in order to make its total number of bonds four. The carbon atom labelled C
1827:
NH in the middle of a chain), some authors allow the group's formula to be stacked vertically whereas others draw an explicit vertical bond within the group.
560:
group is most often written âOH instead of âOâH. These bonds are sometimes drawn out in full in order to accentuate their presence when they participate in
2953:
381:
Carbo- and heterocycles (3- to 8-membered) are generally represented as regular polygons; larger ring sizes tend to be represented by concave polygons.
278:) without explicitly showing the hydrogenâheteroatom bond. Heteroatoms with simple alkyl or aryl substituents, like methoxy (OMe) or dimethylamino (NMe
1513:
An alternate representation that emphasizes this delocalization uses a circle, drawn inside the hexagon of single bonds, to represent the delocalized
2149:
1857:
1429:
1399:
2624:
363:
The linear geometry at sp hybridized atoms is normally depicted by line segments meeting at 180°. Where this involves two double bonds meeting (an
2594:
1546:
766:. However, since the propyl group is monovalent, while praseodymium is nearly always trivalent, ambiguity rarely, if ever, arises in practice.
338:
double bond. Unless all four substituents are explicit, this is true even when stereochemistry is being depicted using wedged or dashed bonds (
1294:. However, tennessine is too unstable to ever be encountered in organic chemistry, so the use of Ts to represent tosyl never causes confusion)
1117:. However, actinium is almost never encountered in organic chemistry, so the use of Ac to represent the acetyl group never causes confusion)
1752:
are generally denoted by dotted or dashed lines. In other contexts, dashed lines may also represent partially formed or broken bonds in a
1385:
exist. In these cases, a combination of solid and dashed lines indicate the integer and non-integer parts of the bond order, respectively.
1793:
double bond within them to be depicted with 150° angles, so that the zigzags on either side of the double bond can propagate horizontally.
2923:
1339:
1589:
1569:
1655:
Hashed wedges or dashed lines (thick or thin) represent bonds that point into the plane of the paper or screen, away from the observer.
1447:
1414:
116:
that make up the molecule. It is represented in two dimensions, as on a piece of paper. It employs certain conventions to represent
2303:
391:
Atoms in a group are ordered so that the bond emanates from the atom that is directly attached to the skeleton. For example, the
2142:
2014:
556:
Lines representing heteroatom-hydrogen bonds are usually omitted for clarity and compactness, so a functional group like the
248:). In fact, skeletal formulae can be thought of as abbreviated Lewis structures that observe the following simplifications:
3075:
1672:
A small filled circle represented an upward pointing hydrogen, while two hash marks represented a downward pointing one.
630:
232:
As in Lewis structures, covalent bonds are indicated by line segments, with a doubled or tripled line segment indicating
691:
Z for conjugating electron-withdrawing groups (in the related MLXZ notation, Z represents a zero-electron donor ligand;
478:
3065:
3008:
2614:
1911:
2270:
1856:
to the stereocenter that gradually become shorter moving away (in analogy to perspective drawing). In the past, the
2135:
2619:
1658:
Wavy lines represent either unknown stereochemistry or a mixture of the two possible stereoisomers at that point.
324:
17:
2327:
1406:
3193:
2609:
1201:
1190:
2296:
2538:
3188:
3183:
2042:
1947:
320:
295:
1652:
Solid wedges represent bonds that point out of the plane of the paper or screen, towards the observer.
2362:
1518:
1505:
is generally depicted as a hexagon with alternating single and double bonds, much like the structure
316:
2387:
2382:
2347:
2312:
2034:
1803:
1087:
1073:
172:
1943:"Graphical representation standards for chemical structure diagrams (IUPAC Recommendations 2008)"
576:
490:
The 3d ball representation of hexane, with carbon (black) and hydrogen (white) shown explicitly.
2958:
2510:
2397:
2289:
2574:
1806:) or polycyclic molecules that cannot be drawn 'flat' without significant distortion (such as
2852:
2665:
2589:
2407:
974:
464:
152:
2118:
3132:
3023:
2847:
2797:
2705:
2690:
2634:
2599:
2495:
2392:
2367:
2234:
2089:
1823:
In cases where the atom has bonds coming from both the left and right (such as a secondary
1553:
1529:
460:
1506:
8:
3112:
2867:
2802:
2639:
2500:
2450:
2445:
2281:
2239:
1710:
176:
2093:
455:
has two bonds to other carbons and is therefore bonded to two hydrogen atoms as well. A
54:
3152:
2812:
2807:
2761:
2751:
2685:
2377:
2352:
2342:
2194:
2059:
2035:"Graphical representation of stereochemical configuration (IUPAC Recommendations 2006)"
572:
561:
519:, and so forth. In the context of organic chemistry, these atoms are commonly known as
168:
164:
101:
89:
3018:
3147:
3097:
3070:
2998:
2877:
2857:
2700:
2505:
2402:
2207:
2184:
2179:
2077:
2010:
1976:
1927:
1907:
1703:
1629:
160:
144:
97:
2063:
147:, partly because they are relatively quick and simple to draw, and also because the
3157:
3142:
3137:
3117:
2968:
2943:
2907:
2902:
2837:
2771:
2675:
2579:
2569:
2543:
2417:
2357:
2332:
2164:
2097:
2051:
1994:
1966:
1956:
1753:
1683:
1318:
1310:
907:
650:
or ligands (in the related MLXZ notation, L represents a two-electron donor ligand)
217:
85:
2584:
415:
128:
3162:
3102:
3013:
2938:
2882:
2832:
2475:
2372:
2260:
2226:
2202:
1737:
1682:
who in 1932 used solid thick lines and dotted lines in a publication. The modern
1621:
1537:
845:
609:
568:
504:
456:
132:
62:
1802:
Smaller rings may also be drawn as concave to show stereochemistry (such as the
596:
3127:
3092:
3033:
2988:
2887:
2872:
2766:
2741:
2695:
2649:
2644:
2480:
2412:
1699:
1661:
An obsolescent depiction of hydrogen stereochemistry that used to be common in
1166:
864:
241:
42:
3177:
3087:
2973:
2897:
2862:
2842:
2746:
2710:
2564:
2548:
2533:
2337:
2080:(2013). "The Historical Origins of Stereochemical Line and Wedge Symbolism".
2002:
1998:
1980:
1749:
1646:
1332:
1160:
622:
148:
2055:
1961:
1942:
127:
An early form of this representation was first developed by organic chemist
3122:
3082:
3003:
2983:
2948:
2933:
2827:
2822:
2792:
2670:
2244:
1687:
1679:
1179:
1014:
763:
731:
675:
58:
46:
2127:
1724:
474:
The skeletal formula of hexane, with carbons number one and three labelled
383:
135:
of molecules and their valence electrons. Hence they are sometimes termed
3107:
3055:
2993:
2963:
2892:
2817:
2787:
2725:
2680:
1742:
1617:
1352:
1094:
960:
928:
788:
737:
693:
in unrelated usage, Z is also an abbreviation for the carboxybenzyl group
686:
392:
237:
233:
221:
201:
2978:
2756:
2720:
2715:
2465:
1811:
1786:
1514:
1382:
1291:
935:
463:(bottom) of the actual molecular structure of hexane, as determined by
268:
261:
194:
50:
2101:
1971:
582:
428:
373:
355:
344:
3060:
3028:
2629:
2604:
2485:
2470:
1274:
1231:
1170:
915:
901:
888:
781:
699:
244:
associated with each atom (although lone pairs are usually optional,
1846:
using the Thiele notation when writing mechanisms (p. 144, 2nd ed.).
1668:
589:
414:, depending on the placement of the bond. In contrast, the isomeric
131:, while the modern form is closely related to and influenced by the
2455:
1435:
1420:
1297:
1224:
1220:
1210:(Ns was the chemical symbol for nielsbohrium, but that was renamed
1194:
1134:
1127:
1114:
1079:
1064:
829:
557:
508:
368:
308:
257:
206:
121:
109:
93:
31:
2928:
2440:
1807:
1691:
1662:
1502:
1471:
1378:
1211:
1123:
1054:
1029:
1003:
991:
805:
724:
706:
679:
626:
542:
503:
All atoms that are not carbon or hydrogen are signified by their
286:
1865:
and a wedged bond and hashed bond with unequal hashes to depict
727:
group (Alk can be used to unambiguously indicate an alkyl group)
2265:
1439:
1108:
985:
946:
882:
874:
753:
667:, when the identities of the ligands are unknown or irrelevant)
647:
524:
516:
512:
444:
364:
210:
117:
37:
906:
Warning: Organometallic chemists often use Np for the related
2435:
1824:
1641:
The relevant chemical bonds can be depicted in several ways:
1281:
966:
720:
658:
571:(middle) and its ball-and-stick model (bottom) of the actual
567:
Shown below for comparison are a skeletal formula (top), its
159:
perspective drawing. Other types of representation, such as
1993:
1533:
Different depictions of chemical bonds in skeletal formulas
994:
group; However, old literature may use Bz for benzyl group.
575:
of the ethanol molecule in the gas phase, as determined by
2311:
498:
2460:
1483:
1020:
151:
notation used for discussions of reaction mechanisms and
30:"Skeletal structure" redirects here. For other uses, see
1186:-bromobenzenesulfonyl) group; OBs is the brosylate group
953:
124:
atoms, which are the most common in organic chemistry.
240:, respectively. Likewise, skeletal formulae indicate
2009:(1st ed.). Oxford University Press. p. 27.
1078:
Cp was the symbol for cassiopeium, a former name for
438:
301:
1678:
An early use of this notation can be traced back to
1694:, and extensively popularised in the 1959 textbook
282:), are sometimes shown in the same way, by analogy.
678:(in some contexts, E is also used to indicate any
1741:Dashed lines (green) to show hydrogen bonding in
1141:-butylcarbonyl) group; OPiv is the pivalate group
179:, the conventions employed also differ somewhat.
3175:
1881:The IUPAC now strongly deprecates this notation.
1374:triple bonds are shown by three parallel lines.
1926:IUPAC Recommendations 1999, Revised Section F:
1390:Examples of multiple bonds in skeletal formulae
447:(top) is shown below. The carbon atom labeled C
143:. Skeletal formulae have become ubiquitous in
92:that serves as a shorthand representation of a
1540:is conveniently denoted in skeletal formulae:
1351:TMS, TBDMS, TES, TBDPS, TIPS, ... for various
661:atom ( is used to indicate a ligated metal, ML
260:carbons are frequently represented by a heavy
2297:
2143:
2028:
2026:
1620:, indicating a mixture of two stereoisomers:
1223:(trifluoromethanesulfonyl) group; OTf is the
1045:the former symbol is derived from the synonym
1043:Tipp for the 2,4,6-triisopropylphenyl group (
294:In the standard depiction of a molecule, the
1154:
482:The Lewis structure of hexane, for reference
477:
427:
382:
372:
354:
343:
2157:
1872:; most others do not make this distinction.
633:, X represents a one-electron donor ligand)
2304:
2290:
2150:
2136:
2023:
1904:General, Organic, and Biological Chemistry
1377:In more advanced theories of bonding, non-
1348:Troc for the trichloroethoxycarbonyl group
914:Câ. Np is also the symbol for the element
1970:
1960:
1495:Represenatations of aromatic benzene ring
608:There are also symbols that appear to be
537:Any hydrogen atoms bonded to heteroatoms
200:The skeleton has hydrogen and/or various
1987:
1736:
1723:
1667:
1528:
1517:. This style, based on one proposed by
1163:in nucleophilic substitution reactions.
999:Dipp for the 2,6-diisopropylphenyl group
603:
112:of a molecule, which is composed of the
49:, featuring skeletal representations of
36:
2032:
1940:
1290:(Ts is also the symbol for the element
1113:(Ac is also the symbol for the element
965:(Ar is also the symbol for the element
499:Explicit heteroatoms and hydrogen atoms
14:
3176:
2076:
1901:
1489:Kekulé style: alternating double bonds
762:Pr is also the symbol for the element
2285:
2131:
1364:THP for the 2-tetrahydropyranyl group
954:Aromatic and unsaturated substituents
443:For example, the skeletal formula of
371:), the bonds are separated by a dot.
1649:in the plane of the paper or screen.
1453:Hex-1-yne has a terminal triple bond
1345:Alloc for the allyloxycarbonyl group
1304:
1193:(methanesulfonyl) group; OMs is the
1150:NPhth for the phthalimide-1-yl group
1101:
1063:An is also the symbol for a generic
1690:to represent the structure of high
887:although Am is also the symbol for
24:
1524:
1234:(nonafluorobutanesulfonyl) group,
615:
595:
588:
581:
485:
469:
439:Implicit carbon and hydrogen atoms
302:Contemporary graphical conventions
227:
27:Representation method in chemistry
25:
3205:
2112:
1732:
1368:
1358:PMB for the 4-methoxybenzyl group
1144:Bt for the 1-benzotriazolyl group
1686:were introduced in the 1940s by
1608:
1588:
1568:
1545:
1482:
1470:
1461:
1446:
1428:
1413:
1398:
2070:
1875:
1849:
1839:
1361:MOM for the methoxymethyl group
1173:groups for further information.
990:not to be confused with Bz for
713:
325:Gesellschaft Deutscher Chemiker
182:
155:can be readily superimposed.
104:. A skeletal formula shows the
1934:
1920:
1895:
1830:
1817:
1796:
1775:
1766:
1023:for phenyl has been in decline
187:
13:
1:
2328:Biological data visualization
2082:Journal of Chemical Education
1929:Replacement of Skeletal Atoms
1888:
1709:Skeletal formulae can depict
1208:-nitrobenzenesulfonyl) group
1147:Im for the 1-imidazolyl group
1804:conformations of cyclohexane
1477:Thiele style: unified circle
467:, are shown for comparison.
41:The skeletal formula of the
7:
1902:Stoker, H. Stephen (2012).
1216:; ONs is the nosylate group
1159:Sulfonate esters are often
1088:pentamethylcyclopentadienyl
534:héteros, meaning "other").
10:
3210:
2368:Mathematical visualization
2043:Pure and Applied Chemistry
2033:Brecher, Jonathan (2006).
1948:Pure and Applied Chemistry
1941:Brecher, Jonathan (2008).
1602:)-2-chloro-2-fluoropentane
1582:)-2-chloro-2-fluoropentane
1562:)-2-chloro-2-fluoropentane
1423:has a terminal double bond
1405:Hex-3-ene has an internal
828:often italicized) for the
321:Royal Society of Chemistry
29:
3046:
2916:
2780:
2734:
2658:
2557:
2526:
2519:
2426:
2363:Information visualization
2348:Educational visualization
2320:
2253:
2225:
2193:
2172:
2163:
2119:Drawing organic molecules
1906:(6th ed.). Cengage.
1440:carbonâcarbon triple bond
1407:carbonâcarbon double bond
1155:Sulfonyl/sulfonate groups
317:American Chemical Society
224:of the organic compound.
2539:Charles-René de Fourcroy
2388:Scientific visualization
2315:of technical information
1863:relative stereochemistry
1759:
1340:fluorenylmethoxycarbonyl
610:chemical element symbols
100:and some details of its
2173:Non-structural formulas
2158:Molecular visualization
2056:10.1351/pac200678101897
1962:10.1351/pac200880020277
1684:solid and hashed wedges
1288:toluenesulfonyl) group
153:electron delocalization
141:LewisâKekulĂ© structures
88:is a type of molecular
2959:Christopher R. Johnson
2511:Technical illustration
2398:Software visualization
1746:
1729:
1728:Alkene stereochemistry
1721:by computer software.
1673:
1645:Solid lines represent
1534:
881:Am for the synonymous
600:
593:
586:
577:microwave spectroscopy
507:, for instance Cl for
491:
483:
475:
432:
387:
377:
359:
348:
315:industry standard (by
311:software package as a
65:
2853:Lawrence J. Rosenblum
2666:Edward Walter Maunder
2590:Charles Joseph Minard
2408:User interface design
2383:Product visualization
1740:
1727:
1671:
1532:
629:atom (in the related
604:Pseudoelement symbols
599:
592:
585:
541:drawn explicitly. In
489:
481:
473:
465:X-ray crystallography
431:
386:
376:
358:
347:
40:
3133:Scientific modelling
3108:Information graphics
2848:Clifford A. Pickover
2798:William S. Cleveland
2706:Henry Norris Russell
2691:Howard G. Funkhouser
2635:Florence Nightingale
2600:Francis Amasa Walker
2496:Statistical graphics
2418:Volume visualization
2393:Social visualization
2235:Ball-and-stick model
1616:Skeletal formula of
1596:Skeletal formula of
1576:Skeletal formula of
1554:Ball-and-stick model
1165:See the articles on
461:ball-and-stick model
3194:Chemical structures
3113:Information science
3076:in computer science
2868:Sheelagh Carpendale
2803:George G. Robertson
2640:Karl Wilhelm Pohlke
2575:André-Michel Guerry
2451:Graph of a function
2446:Engineering drawing
2240:Space-filling model
2195:Structural formulas
2094:2013JChEd..90..676J
1057:group, usually the
1032:group, usually the
562:reaction mechanisms
177:inorganic chemistry
3153:Volume cartography
2917:Early 21st century
2813:Catherine Plaisant
2808:Bruce H. McCormick
2762:Mary Eleanor Spear
2752:Arthur H. Robinson
2686:Arthur Lyon Bowley
2659:Early 20th century
2506:Technical drawings
2378:Molecular graphics
2353:Flow visualization
2343:Data visualization
2078:Jensen, William B.
1785:-olefins (such as
1747:
1730:
1674:
1535:
1126:group; OBz is the
723:group or even any
601:
594:
587:
492:
484:
476:
433:
388:
378:
360:
349:
169:Fischer projection
165:Haworth projection
106:skeletal structure
102:molecular geometry
90:structural formula
74:line-angle formula
66:
3189:Chemical formulas
3184:Organic chemistry
3171:
3170:
3148:Visual perception
3098:Graphic organizer
3071:Computer graphics
3042:
3041:
3024:Martin Wattenberg
2999:Hanspeter Pfister
2954:Martin Krzywinski
2878:Jock D. Mackinlay
2858:Thomas A. DeFanti
2781:Late 20th century
2701:Ejnar Hertzsprung
2403:Technical drawing
2279:
2278:
2221:
2220:
2208:Condensed formula
2185:Molecular formula
2180:Empirical formula
2165:Chemical formulas
2102:10.1021/ed200177u
2050:(10): 1897â1970.
2016:978-0-19-850346-0
2007:Organic Chemistry
1997:; Greeves, Nick;
1995:Clayden, Jonathan
1704:George S. Hammond
1696:Organic Chemistry
1501:In recent years,
1305:Protecting groups
1102:Functional groups
530:comes from Greek
218:functional groups
161:Newman projection
145:organic chemistry
137:Kekulé structures
82:shorthand formula
78:bond-line formula
16:(Redirected from
3201:
3158:Volume rendering
3143:Visual analytics
3138:Spatial analysis
3118:Misleading graph
2969:David McCandless
2944:Gordon Kindlmann
2908:Alfred Inselberg
2903:Leland Wilkinson
2838:Michael Friendly
2772:Howard T. Fisher
2735:Mid 20th century
2676:W. E. B. Du Bois
2580:William Playfair
2570:Adolphe Quetelet
2544:Joseph Priestley
2527:Pre-19th century
2524:
2523:
2491:Skeletal formula
2358:Geovisualization
2333:Chemical imaging
2306:
2299:
2292:
2283:
2282:
2227:Molecular models
2213:Skeletal formula
2170:
2169:
2152:
2145:
2138:
2129:
2128:
2106:
2105:
2074:
2068:
2067:
2039:
2030:
2021:
2020:
1991:
1985:
1984:
1974:
1964:
1938:
1932:
1924:
1918:
1917:
1899:
1882:
1879:
1873:
1853:
1847:
1843:
1837:
1834:
1828:
1821:
1815:
1800:
1794:
1789:), allowing the
1779:
1773:
1770:
1754:transition state
1612:
1592:
1572:
1549:
1486:
1474:
1450:
1438:has an internal
1432:
1417:
1402:
1311:protecting group
1272:
1271:
1270:
1262:
1261:
1253:
1252:
1244:
1243:
1074:cyclopentadienyl
1065:actinoid element
425:
421:
413:
405:
256:, while (hetero)
86:organic compound
70:skeletal formula
21:
3209:
3208:
3204:
3203:
3202:
3200:
3199:
3198:
3174:
3173:
3172:
3167:
3163:Information art
3103:Imaging science
3048:
3038:
3019:Fernanda Viégas
3014:Moritz Stefaner
2939:Jessica Hullman
2912:
2883:Alan MacEachren
2833:Ben Shneiderman
2776:
2730:
2654:
2553:
2515:
2428:
2422:
2373:Medical imaging
2316:
2310:
2280:
2275:
2261:Molecular graph
2249:
2217:
2203:Lewis structure
2189:
2159:
2156:
2123:chemguide.co.uk
2115:
2110:
2109:
2075:
2071:
2037:
2031:
2024:
2017:
1992:
1988:
1939:
1935:
1925:
1921:
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1900:
1896:
1891:
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1885:
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1876:
1870:stereochemistry
1854:
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1577:
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1564:
1563:
1557:
1550:
1538:Stereochemistry
1527:
1525:Stereochemistry
1519:Johannes Thiele
1499:
1498:
1497:
1496:
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1237:
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1157:
1104:
956:
913:
716:
666:
645:
618:
616:General symbols
606:
569:Lewis structure
552:
548:
505:chemical symbol
501:
457:Lewis structure
454:
450:
441:
436:
423:
419:
411:
407:
404:
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398:
304:
281:
277:
255:
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228:Basic structure
190:
185:
133:Lewis structure
63:stereochemistry
35:
28:
23:
22:
18:Carbon skeleton
15:
12:
11:
5:
3207:
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3128:Patent drawing
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3093:Graphic design
3090:
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3068:
3063:
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3044:
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3034:Hadley Wickham
3031:
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3016:
3011:
3006:
3001:
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2989:Tamara Munzner
2986:
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2888:David Goodsell
2885:
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2873:Cynthia Brewer
2870:
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2775:
2774:
2769:
2767:Edgar Anderson
2764:
2759:
2754:
2749:
2744:
2742:Jacques Bertin
2738:
2736:
2732:
2731:
2729:
2728:
2723:
2718:
2713:
2708:
2703:
2698:
2696:John B. Peddle
2693:
2688:
2683:
2678:
2673:
2668:
2662:
2660:
2656:
2655:
2653:
2652:
2650:Francis Galton
2647:
2645:Toussaint Loua
2642:
2637:
2632:
2627:
2625:Georg von Mayr
2622:
2617:
2615:Matthew Sankey
2612:
2607:
2602:
2597:
2592:
2587:
2582:
2577:
2572:
2567:
2561:
2559:
2555:
2554:
2552:
2551:
2546:
2541:
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2530:
2528:
2521:
2517:
2516:
2514:
2513:
2508:
2503:
2498:
2493:
2488:
2483:
2481:Sankey diagram
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2432:
2430:
2424:
2423:
2421:
2420:
2415:
2413:Visual culture
2410:
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2385:
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2205:
2199:
2197:
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2182:
2176:
2174:
2167:
2161:
2160:
2155:
2154:
2147:
2140:
2132:
2126:
2125:
2114:
2113:External links
2111:
2108:
2107:
2088:(5): 676â677.
2069:
2022:
2015:
2003:Wothers, Peter
1999:Warren, Stuart
1986:
1955:(2): 277â410.
1933:
1919:
1913:978-1133103943
1912:
1893:
1892:
1890:
1887:
1884:
1883:
1874:
1848:
1838:
1829:
1816:
1795:
1774:
1764:
1763:
1761:
1758:
1750:Hydrogen bonds
1734:
1733:Hydrogen bonds
1731:
1700:Donald J. Cram
1676:
1675:
1659:
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1404:
1397:
1394:
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1389:
1388:
1387:
1370:
1369:Multiple bonds
1367:
1366:
1365:
1362:
1359:
1356:
1349:
1346:
1343:
1336:
1325:
1322:butoxycarbonyl
1306:
1303:
1302:
1301:
1278:
1267:
1258:
1249:
1240:
1228:
1217:
1198:
1187:
1161:leaving groups
1156:
1153:
1152:
1151:
1148:
1145:
1142:
1131:
1120:
1103:
1100:
1099:
1098:
1091:
1084:
1070:
1051:
1037:
1026:
1007:
1000:
997:
978:
975:heteroaromatic
971:
955:
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939:
932:
921:
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894:
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813:
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300:
296:canonical form
292:
291:
285:Lone pairs on
283:
279:
275:
272:
265:
253:
242:formal charges
238:triple bonding
229:
226:
189:
186:
184:
181:
173:organometallic
114:skeletal atoms
43:antidepressant
26:
9:
6:
4:
3:
2:
3206:
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3114:
3111:
3109:
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3101:
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3091:
3089:
3088:Graph drawing
3086:
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3057:
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3035:
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3017:
3015:
3012:
3010:
3009:Claudio Silva
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
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2974:Mauro Martino
2972:
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2899:
2898:Michael Maltz
2896:
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2889:
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2876:
2874:
2871:
2869:
2866:
2864:
2863:George Furnas
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2843:Howard Wainer
2841:
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2747:Rudolf Modley
2745:
2743:
2740:
2739:
2737:
2733:
2727:
2724:
2722:
2719:
2717:
2714:
2712:
2711:Max O. Lorenz
2709:
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2623:
2621:
2620:Charles Booth
2618:
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2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2595:Luigi Perozzo
2593:
2591:
2588:
2586:
2585:August Kekulé
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2566:
2565:Charles Dupin
2563:
2562:
2560:
2556:
2550:
2549:Gaspard Monge
2547:
2545:
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2540:
2537:
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2534:Edmond Halley
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2338:Crime mapping
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2325:
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2319:
2314:
2313:Visualization
2307:
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2018:
2012:
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1982:
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1338:Fmoc for the
1337:
1334:
1333:carboxybenzyl
1330:
1326:
1323:
1321:
1316:
1315:
1314:
1312:
1299:
1296:; OTs is the
1295:
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1279:
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979:
976:
972:
970:
968:
962:
958:
957:
948:
944:
940:
937:
934:Ad for the 1-
933:
930:
926:
922:
919:
917:
909:
903:
899:
895:
892:
890:
884:
880:
876:
872:
869:
867:
862:
860:
856:
853:
850:
848:
843:
841:
837:
834:
831:
827:
823:
821:
817:
814:
811:
809:
803:
801:
797:
793:
790:
786:
783:
779:
777:
773:
770:
767:
765:
759:
757:
751:
749:
745:
741:
739:
735:
733:
729:
726:
722:
718:
717:
708:
704:
701:
697:
694:
690:
688:
684:
681:
677:
673:
669:
665:
660:
656:
652:
649:
644:
639:
635:
632:
631:MLXZ notation
628:
624:
620:
619:
613:
611:
598:
591:
584:
580:
578:
574:
570:
565:
563:
559:
554:
544:
540:
535:
533:
529:
526:
522:
518:
514:
510:
506:
496:
488:
480:
472:
468:
466:
462:
459:(middle) and
458:
446:
430:
417:
416:nitrite group
394:
390:
385:
380:
375:
370:
366:
362:
357:
351:
346:
341:
337:
332:
331:
329:
326:
322:
318:
314:
310:
299:
297:
288:
284:
273:
270:
266:
263:
259:
251:
250:
249:
247:
243:
239:
235:
225:
223:
219:
214:
212:
208:
203:
198:
196:
180:
178:
174:
170:
166:
162:
156:
154:
150:
146:
142:
138:
134:
130:
129:August Kekulé
125:
123:
119:
115:
111:
107:
103:
99:
95:
91:
87:
83:
79:
75:
71:
64:
60:
59:phenyl groups
56:
52:
48:
44:
39:
33:
19:
3123:Neuroimaging
3083:CPK coloring
3066:Color coding
3004:Hans Rosling
2984:Miriah Meyer
2949:Aaron Koblin
2934:Jeffrey Heer
2828:Edward Tufte
2823:Pat Hanrahan
2793:Nigel Holmes
2671:Otto Neurath
2610:Oliver Byrne
2558:19th century
2490:
2245:CPK coloring
2212:
2122:
2085:
2081:
2072:
2047:
2041:
2006:
1989:
1952:
1946:
1936:
1928:
1922:
1903:
1897:
1877:
1869:
1866:
1862:
1851:
1841:
1832:
1819:
1798:
1790:
1782:
1777:
1768:
1748:
1715:
1711:
1708:
1695:
1688:Giulio Natta
1680:Richard Kuhn
1677:
1640:
1631:
1623:
1599:
1579:
1559:
1536:
1512:
1500:
1376:
1372:
1328:
1319:
1317:Boc for the
1308:
1289:
1285:
1209:
1205:
1183:
1164:
1158:
1138:
1133:Piv for the
1112:
1086:Cp* for the
1077:
1062:
1058:
1047:
1044:
1040:
1033:
1028:Tol for the
1018:
1015:phenyl group
1010:
1002:Mes for the
989:
984:Bzl for the
981:
973:Het for any
964:
963:substituent
945:Trt for the
942:
927:Chx for the
924:
905:
900:Neo for the
897:
886:
878:
865:
861:
858:
854:
846:
842:
839:
835:
825:
822:
819:
815:
807:
802:
799:
795:
787:All for the
778:
775:
771:
764:praseodymium
761:
755:
750:
747:
743:
732:methyl group
714:Alkyl groups
692:
676:electrophile
671:
663:
657:Met for any
654:
642:
637:
607:
573:3D structure
566:
555:
538:
536:
531:
527:
520:
502:
493:
442:
339:
335:
312:
305:
293:
245:
231:
215:
202:substituents
199:
191:
183:The skeleton
157:
149:curved arrow
140:
136:
126:
113:
105:
81:
77:
73:
69:
67:
47:escitalopram
3056:Cartography
2994:Ade Olufeko
2964:Manuel Lima
2893:Kwan-Liu Ma
2818:Stuart Card
2788:Borden Dent
2726:Erwin Raisz
2681:Henry Gantt
1743:acetic acid
1618:amphetamine
1353:silyl ether
1230:Nf for the
1219:Tf for the
1200:Ns for the
1189:Ms for the
1178:Bs for the
1122:Bz for the
1107:Ac for the
1095:vinyl group
1093:Vi for the
1072:Cp for the
1053:An for the
1019:the use of
977:substituent
959:Ar for any
910:group, PhMe
873:Pn for the
863:Bu for the
844:Bu for the
804:Bu for the
789:allyl group
780:Pr for the
752:Pr for the
738:ethyl group
736:Et for the
730:Me for the
687:nucleophile
685:Nu for any
674:El for any
621:X for any (
521:heteroatoms
418:is denoted
399:is denoted
393:nitro group
222:hydrocarbon
195:heteroatoms
188:Terminology
55:triple bond
51:heteroatoms
3178:Categories
2979:John Maeda
2757:John Tukey
2721:Harry Beck
2716:Fritz Kahn
2466:Photograph
2254:Other ways
1972:10092/2052
1889:References
1812:adamantane
1787:oleic acid
1515:pi orbital
1383:bond order
1381:values of
1331:Z for the
1292:tennessine
1097:(uncommon)
1013:Ï for the
929:cyclohexyl
791:(uncommon)
719:R for any
269:octet rule
262:center dot
209:, "O" for
3061:Chartjunk
3029:Bang Wong
2924:Polo Chau
2630:John Snow
2605:John Venn
2486:Schematic
2471:Pictogram
1981:1365-3075
1436:Hex-3-yne
1421:Hex-1-ene
1275:nonaflate
1171:sulfonate
936:adamantyl
916:neptunium
902:neopentyl
889:americium
847:secondary
782:isopropyl
700:deuterium
515:, Na for
340:see below
246:see below
3047:Related
2456:Ideogram
2064:97528124
2005:(2001).
1867:absolute
1692:polymers
1298:tosylate
1232:nonaflyl
1225:triflate
1195:mesylate
1167:sulfonyl
1128:benzoate
1115:actinium
1080:lutetium
1061:isomer (
961:aromatic
866:tertiary
830:isobutyl
758:) propyl
682:element)
558:hydroxyl
511:, O for
509:chlorine
369:cumulene
313:de facto
309:ChemDraw
258:cumulene
213:, etc.)
207:nitrogen
122:hydrogen
110:skeleton
94:molecule
32:Skeleton
2929:Ben Fry
2441:Diagram
2090:Bibcode
1808:tropane
1718:isomers
1663:steroid
1503:benzene
1379:integer
1280:Ts for
1221:triflyl
1212:bohrium
1135:pivalyl
1124:benzoyl
1076:group (
1009:Ph, Ί,
1004:mesityl
992:benzoyl
988:group (
908:neophyl
904:group (
885:group,
877:group (
810:) butyl
760:group (
725:organyl
707:tritium
680:p-block
627:halogen
543:ethanol
528:hetero-
287:carbene
98:bonding
3049:topics
2520:People
2427:Image
2321:Fields
2266:SMILES
2062:
2013:
1979:
1910:
1507:Kekulé
1355:groups
1180:brosyl
1111:group
1109:acetyl
1055:anisyl
1048:isityl
1036:isomer
986:benzyl
947:trityl
875:pentyl
808:normal
756:normal
705:T for
698:D for
648:ligand
646:for a
623:pseudo
532:áŒÏΔÏÎżÏ
525:prefix
517:sodium
513:oxygen
445:hexane
365:allene
323:, and
290:shown.
234:double
211:oxygen
118:carbon
84:of an
2501:Table
2436:Chart
2429:types
2271:InChl
2121:from
2060:S2CID
2038:(PDF)
1858:IUPAC
1825:amine
1760:Notes
1716:trans
1647:bonds
1342:group
1335:group
1324:group
1300:group
1282:tosyl
1277:group
1227:group
1214:, Bh)
1202:nosyl
1197:group
1191:mesyl
1130:group
1090:group
1030:tolyl
1006:group
967:argon
949:group
938:group
931:group
870:group
868:butyl
851:group
849:butyl
832:group
812:group
784:group
746:-Pr,
721:alkyl
659:metal
523:(the
45:drug
2476:Plot
2011:ISBN
1977:ISSN
1908:ISBN
1810:and
1714:and
1702:and
1628:and
1327:Cbz
1169:and
1059:para
1034:para
883:amyl
857:-Bu
838:-Bu
824:Bu (
818:-Bu
798:-Bu
794:Bu,
774:-Pr
742:Pr,
424:ONOâ
420:âONO
175:and
120:and
68:The
61:and
53:, a
2461:Map
2098:doi
2052:doi
1967:hdl
1957:doi
1791:cis
1783:cis
1712:cis
1698:by
1556:of
1245:(CF
1039:Is
1021:phi
980:Bn
941:Tr
923:Cy
896:Np
709:(H)
702:(H)
545:, C
539:are
422:or
406:or
401:âNO
367:or
342:).
336:cis
236:or
167:or
139:or
108:or
96:'s
80:or
3180::
2096:.
2086:90
2084:.
2058:.
2048:78
2046:.
2040:.
2025:^
2001:;
1975:.
1965:.
1953:80
1951:.
1945:.
1814:).
1756:.
1706:.
1634:)-
1626:)-
1329:or
1320:t-
1309:A
1286:p-
1263:SO
1236:CF
1041:or
1011:or
982:or
943:or
925:or
898:or
879:or
859:or
840:or
820:or
800:or
776:or
748:or
695:.)
672:or
670:E
655:or
653:M
638:or
636:L
579:.
564:.
426:.
412:Nâ
395:NO
319:,
197:.
163:,
76:,
72:,
57:,
2305:e
2298:t
2291:v
2151:e
2144:t
2137:v
2104:.
2100::
2092::
2066:.
2054::
2019:.
1983:.
1969::
1959::
1916:.
1745:.
1632:S
1630:(
1624:R
1622:(
1600:S
1598:(
1580:R
1578:(
1560:R
1558:(
1284:(
1268:2
1259:3
1254:)
1250:2
1241:3
1206:p
1204:(
1184:p
1182:(
1139:t
1137:(
1119:;
1083:)
1069:)
1050:)
1025:)
1017:(
996:)
920:)
918:.
912:2
893:)
891:.
855:t
836:s
826:i
816:i
806:(
796:n
772:i
768:)
754:(
744:n
664:n
643:n
640:L
625:)
551:5
549:H
547:2
453:3
449:1
410:2
408:O
403:2
397:2
280:2
276:2
264:.
254:3
34:.
20:)
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