Investigation of C–H⋯X (X=N, O, S) intramolecular hydrogen bond in 1-vinyl-2-(2′-heteroaryl)pyrroles by ab initio calculations
The C–H⋯X (X=N, O, S) intramolecular hydrogen bond between the α-hydrogen of the vinyl group and the corresponding heteroatom in the series of 1-vinyl-2-(2′-heteroaryl)pyrroles was examined by ab initio calculations at the B3LYP/6-311(d,p) level. It was shown that the C–H⋯N hydrogen bond is stronger...
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Published in | Journal of molecular structure. Theochem Vol. 680; no. 1; pp. 127 - 135 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Elsevier B.V
05.07.2004
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Subjects | |
Online Access | Get full text |
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Summary: | The C–H⋯X (X=N, O, S) intramolecular hydrogen bond between the α-hydrogen of the vinyl group and the corresponding heteroatom in the series of 1-vinyl-2-(2′-heteroaryl)pyrroles was examined by ab initio calculations at the B3LYP/6-311(d,p) level. It was shown that the C–H⋯N hydrogen bond is stronger than the C–H⋯O hydrogen bond and the latter is, in turn, stronger than the C–H⋯S hydrogen bond. This conclusion is supported by calculations of
1H NMR chemical shieldings. |
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ISSN: | 0166-1280 1872-7999 |
DOI: | 10.1016/j.theochem.2004.02.020 |