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Study of the structure of besulpamide, 1‐[(4‐chloro‐3‐sulfamoylbenzoyl)amino]2,4,6‐trimethylpyridinium hydroxide inner salt, and related compounds, using X‐Ray crystallography and 1 H and 13 C nuclear magnetic resonance spectroscopy
Author(s) -
Frigola Jordi
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260527
Subject(s) - chemistry , salt (chemistry) , crystal structure , tautomer , crystallography , nuclear magnetic resonance spectroscopy , hydroxide , mass spectrometry , spectroscopy , stereochemistry , inorganic chemistry , physics , chromatography , quantum mechanics
The diuretic and antihypertensive drug Besulpamide, 1‐[(4‐Chloro‐3‐sulfamoylbenzoyl)amino]‐2,4,6‐trimethylpyridinium hydroxide inner salt, and related compounds have been investigated by nmr spectroscopy and mass spectrometry. A mechanism for the formation of the salt 5 is proposed. The tautomerism of hydroxy derivatives of Besulpamide is discussed on the basis of nmr spectroscopy. The single‐crystal X‐ray investigation of Besulpamide, R = 0.038 (R w = 0.041), showed two crystallographically independent molecular conformations in the crystal structure, space group P \documentclass{article}\pagestyle{empty}\begin{document}$\bar 1$\end{document} , a = 8.485(3), b = 14.282(2), c = 15.312(6), α = 69.41(2), β = 82.22(4), γ = 72.78(3).