Knowledge

Cyanocarbon

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Webster, Owen W. "Cyanocarbons: a classic example of discovery-driven research" Journal of Polymer Science, Part A: Polymer Chemistry 2001, volume, 40, pp. 210-221.
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Cyanocarbons are organic compounds bearing enough cyano functional groups to significantly alter their chemical properties.
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Middleton, W. J.; Wiley, D. W. (1961). "Tetramethylammonium 1,1,2,3,3-Pentacyanopropenide".
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tend to be stronger than the parents. The cyanide group can also stabilize anions by
59: 28: 20: 298: 267: 240: 213: 36: 32: 62:, also known as carbon tetracyanide). Organic chemists often refer to cyanides as 120: 82: 74: 70: 302: 345: 271: 244: 40: 217: 168: 290: 110: 44: 162: 127: 63: 48: 109:, which reduces to a stable anion , unlike most derivatives of 73:
substituent. Thus, for example, cyanide-substituted
119:, which forms an air-stable anion, in contrast to 343: 229:Linn, W. J. (1969). "Tetracyanoethylene Oxide". 161:, which reduces to a stable anion, unlike most 257: 130:that undergoes ready scission of its C-C bond. 35:. Such substances generally are classified as 326: 16:Class of organic compounds containing cyanide 228: 126:Tetracyanoethylene oxide, an electrophilic 333: 319: 92: 39:, since they are formally derived from 344: 222: 208: 206: 51:group. One of the simplest member is 285: 13: 203: 14: 368: 289: 251: 1: 196: 31:that contain several cyanide 305:. You can help Knowledge by 7: 102:Illustrative cyanocarbons: 10: 373: 284: 69:In general, cyanide is an 117:Pentacyanocyclopentadiene 43:by replacing one or more 272:10.15227/orgsyn.041.0099 245:10.15227/orgsyn.049.0103 134:Tetracyanoquinodimethane 93:Definition and examples 357:Organic compound stubs 297:This article about an 180:Pentacyanopropenide, 171:(tricyanomethane), 218:10.1002/pola.10087 107:Tetracyanoethylene 29:chemical compounds 314: 313: 232:Organic Syntheses 60:tetracyanomethane 37:organic compounds 33:functional groups 21:organic chemistry 364: 335: 328: 321: 299:organic compound 293: 286: 276: 275: 255: 249: 247: 226: 220: 210: 191: 177: 160: 75:carboxylic acids 57: 372: 371: 367: 366: 365: 363: 362: 361: 342: 341: 340: 339: 282: 280: 279: 256: 252: 227: 223: 211: 204: 199: 189: 185: 181: 176: 172: 159: 155: 145: 141: 137: 121:cyclopentadiene 95: 85:as revealed by 71:electronegative 56: 52: 27:are a group of 17: 12: 11: 5: 370: 360: 359: 354: 338: 337: 330: 323: 315: 312: 311: 294: 278: 277: 250: 221: 201: 200: 198: 195: 194: 193: 187: 183: 178: 174: 166: 157: 153: 143: 139: 131: 124: 114: 94: 91: 54: 15: 9: 6: 4: 3: 2: 369: 358: 355: 353: 350: 349: 347: 336: 331: 329: 324: 322: 317: 316: 310: 308: 304: 300: 295: 292: 288: 287: 283: 273: 269: 265: 261: 254: 246: 242: 238: 234: 233: 225: 219: 215: 209: 207: 202: 186:C=C(CN)−C(CN) 179: 170: 167: 164: 151: 150: 135: 132: 129: 125: 122: 118: 115: 112: 108: 105: 104: 103: 100: 99: 90: 88: 84: 80: 76: 72: 67: 65: 61: 50: 47:atoms with a 46: 42: 38: 34: 30: 26: 22: 307:expanding it 296: 281: 263: 259: 253: 236: 230: 224: 148: 101: 97: 96: 89:structures. 79:delocalizing 68: 41:hydrocarbons 25:cyanocarbons 24: 18: 346:Categories 260:Org. Synth 197:References 182:[(NC) 169:Cyanoform 87:resonance 81:negative 352:Nitriles 163:quinones 111:ethylene 64:nitriles 45:hydrogen 239:: 103. 152:-(C(CN) 128:epoxide 49:cyanide 266:: 99. 173:HC(CN) 83:charge 301:is a 53:C(CN) 303:stub 149:para 268:doi 241:doi 214:doi 19:In 348:: 264:41 262:. 237:49 235:. 205:^ 136:, 66:. 23:, 334:e 327:t 320:v 309:. 274:. 270:: 248:. 243:: 216:: 192:. 190:] 188:2 184:2 175:3 165:. 158:2 156:) 154:2 146:- 144:4 142:H 140:6 138:C 123:. 113:. 58:( 55:4

Index

organic chemistry
chemical compounds
functional groups
organic compounds
hydrocarbons
hydrogen
cyanide
tetracyanomethane
nitriles
electronegative
carboxylic acids
delocalizing
charge
resonance
Tetracyanoethylene
ethylene
Pentacyanocyclopentadiene
cyclopentadiene
epoxide
Tetracyanoquinodimethane
para
quinones
Cyanoform


doi
10.1002/pola.10087
Organic Syntheses
doi
10.15227/orgsyn.049.0103

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