FTIR Spectral Study of Intramolecular Hydrogen Bonding in Thromboxane A2Receptor Antagonist S-145 and Related Compounds. Part 4
- 1 July 1993
- journal article
- research article
- Published by Taylor & Francis in Spectroscopy Letters
- Vol. 26 (6) , 1023-1037
- https://doi.org/10.1080/00387019308011590
Abstract
An N-methylated compound of S-145, (±)-(5Z)-7-[3-endo-[N-methyl)phenylsulphonyl)amino]bicyclo [2.2.1]hept-2-exo-yl]heptenoic acid 1, its chain analogue 12-[N-methyl(phenylsulphonyl)amino]dodecanoic acid 3, (±)-(5Z)-7-[3-endo-(benzoylamino)bicyclo[2.2.1]hept-2-exo-yl] heptenoic acid 5 and related compounds were synthesized in order to study the formation of a new class of intramolecular hydrogen bond IX (cis-CO2H…O = Y). Their FTIR spectra were measured in dilute CCl4 solution and subjected to curve analysis in order to separate overlapping absorption bands. For compounds 1,3 and 5, the intramolecular hydrogen bonds of the IX type involving 14-, 17- and 14-membered rings were found between a carboxyl group, which takes a cis-structure IV, and an oxygen atom of a sulphonyl or benzoylamino group, respectively. The C[dbnd]O stretching vibration bands of these carboxyl groups shifted to lower wavenumbers (ca. 19 cm−1). The direction of these shifts was contrary to that found for α-keto and α-alkoxycarboxylic acids in which carboxyl groups take a trans-structure III due to the formation of intramolecular hydrogen bonds I and II, respectively.Keywords
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