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preface to fifteenth edition

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PROPERTIES OF ATOMS, RADICALS, AND BONDS 4.37<br />

TABLE 4.9<br />

Bond Lengths between Carbon and Other Elements (Continued)<br />

Bond type<br />

Bond length, pm<br />

Carbon-hydrogen<br />

Paraffinic<br />

In methane (in CD 4 , 109.2) 109.4<br />

In monosubstituted carbon: H9C9Y 109.6(5)<br />

X<br />

In disubstituted carbon:<br />

H9C9<br />

Y<br />

X<br />

107.3(5)<br />

In trisubstituted carbon: H9C9Y<br />

107.0(7)<br />

Olefinic<br />

Z<br />

Simple: H9C"C9 108.3(5)<br />

Cumulative carbon-carbon double bonds: H9C"C"C9 107(1)<br />

Cumulative carbon-carbon-oxygen double bonds: H9C9C"C"O 108(1)<br />

Aromatic 108.4(5)<br />

Acetylenic (in C 2 H 2 , 105.9) 105.5(5)<br />

In small rings 108.1(5)<br />

In presence of a carbon triple bond: H9C#C9 111.5(4)<br />

Carbon-nitrogen<br />

Single bond<br />

Paraffinic:<br />

3-covalent nitrogen: RNH 2 ,R 2 NH, R 3 N 147.2(5)<br />

<br />

4-covalent nitrogen: RNH 3 , R 3 N-BX 3<br />

147.9(5)<br />

In 9C9N" 147.5(10)<br />

In aromatic compounds 143(1)<br />

In conjugated heterocyclic systems (partial double bond) 135.3(5)<br />

In 9N9C"O (partial double bond) 132.2(5)<br />

Double bond: 9C"N9 132<br />

Triple bond (in CN radical, 117.74): 9C#N 115.7(5)<br />

Carbon-oxygen<br />

Single bond<br />

Paraffinic and saturated heterocyclic: 9C9O9 142.6(5)<br />

Strained, as in epoxides: 9C9C9<br />

143.5(5)<br />

O<br />

In aromatic compounds, as Ar-OH 136(1)<br />

Longer bond in carboxylic acids and esters (HCOOH, 131.2) 135.8(5)<br />

In conjugated heterocyclics, as furan 137.1(16)<br />

Double bond<br />

In CO 111.5<br />

In CO 112.8<br />

<br />

In CO 2 117.7<br />

In HCO 119.8(8)<br />

In carbonyls 114.5(10)<br />

In aldehydes and ke<strong>to</strong>nes 121.5(5)

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