ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The carbonyl group in lactones and, to a lesser extent, in lactams tends to show a C—C=O angle that is larger than the O—C=O or N—C=O angle, the difference increasing in magnitude as the ring size decreases. The observed trend provides information on ratios of force constants characterising the flexibility of the s-cis-ester group and may be interpreted in terms of incipient chemical reaction to -O—(CH2)n—C≡O+. Molecular orbital calculations (MINDO/3, MNDO, EH) for model compounds provide an electronic interpretation of this angle difference in terms of an anomeric interaction between the p-type lone pair on the carbonyl O-atom and the antibonding C-O or C-N orbital.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680110
