-CO-NH- (peptide bond): which statement is incorrect about peptide bond : -

$-CO-NH-$ (peptide bond): which statement is incorrect about peptide bond : -
A C–N bond length in proteins is longer than usual bond length of C–N bond
B Spectroscopic analysis shows planar structure of the $-CO-NH-$ group
C C–N bond length in proteins is smaller than usual bond length of C–N bond
D None of above

Detailed Solution

In the peptide group, the lone pair on nitrogen is delocalised into the carbonyl group (resonance): $-C(=O)-NH- \leftrightarrow -C(-O^-)=NH^+-$.
So the C–N bond has partial double bond character. Its length (about 1.32 Å) is shorter than a normal C–N single bond (about 1.47 Å).
Because of this partial double bond, rotation about C–N is restricted and the $-CO-NH-$ group is planar, as shown by spectroscopy and X-ray studies.
So the statement that the C–N bond length in proteins is longer than the usual C–N bond length is incorrect.

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