NDLI: On the Relative Importance of O–H/π Interactions in 7-Norbornenols

Content Provider	Springer Nature Link
Author	Marchand, Alan P. Ganguly, Bishwajit
Copyright Year	2000
Abstract	The geometries of the two H–O–C rotamers of synand two of anti-7-norbornenol have been optimized at the ab initio HF/6-31G and B3LYP hybrid HF-DFT levels of theory by using a 6-31G basis set. Contrary to an earlier report, we find that the (nongeometry constrained) anti-trans isomer (1d) is predicted to be more stable than the corresponding syn-cis form (1a). The increased stability of 1d vis-à-vis 1a can be accounted for in terms of relative H(1)–C(2)–O(3)–H(4) torsion energy effects. The computational results indicate that the hydroxyl proton in 1a enters into intramolecular hydrogen bonding with the proximate C=C π bond. Supporting evidence for this conclusion resides in the fact that the 1a is predicted to possess the lowest O–H stretching frequency, a result that can be attributed to π-hydrogen bonding.
Starting Page	241
Ending Page	244
Page Count	4
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	11
Issue Number	4
e-ISSN	15729001
Language	English
Publisher	Kluwer Academic Publishers-Plenum Publishers
Publisher Date	2000-01-01
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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On the Relative Importance of O–H/π Interactions in 7-Norbornenols