Question
Which statement about peptide bonds is NOT true?
C–N bond length in proteins is longer than the usual bond length of the C–N single bond.
Spectroscopic analysis shows the planar structure of the peptide group.
C–N bond length in proteins is smaller than the usual bond length of the C–N single bond.
None of the above.
Proteins are linear polymers of amino acids linked together by peptide bonds . A peptide bond (–CO–NH–) exhibits resonance, where the lone pair of electrons on the nitrogen atom is delocalised into the carbonyl group . This resonance gives the C–N bond partial double bond character . According to the principles of chemical bonding, bond lengths in resonance hybrids are intermediate between single and double bonds . Specifically, as bond order increases, bond length decreases . In the sources, a typical C–N single bond length is 143 pm, while a C=N double bond is 138 \pm . Due to its partial double bond character, the C–N bond in a peptide is shorter (typically around 132 pm) than a standard C–N single bond . Therefore, the statement that the bond is longer is incorrect. Additionally, this resonance restricts rotation about the bond, resulting in a planar geometry for the peptide group .
This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Organic Chemistry – Some Basic Principles and Techniques . Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.
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