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Figure 9
Resonance models of an N-acetyl side chain (a) in vacuo and in nonpolar solvents, and (b) in polar and/or hydrogen-bonding solvents. In part (b), the hydrogen bond to the carbonyl O atom shifts the relative con­tributions of the resonance forms towards those bearing a C=N double bond. Participation of the N—H hydrogen as a hydrogen-bond donor appears to exert weaker but reinforcing effects on the C—N and C—O bond lengths (see Table 1[link]).

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 76| Part 3| March 2020| Pages 287-297
https://doi.org/10.1107/S2053229620001515
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