๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Hydrogen bonding in sulfonamides

โœ Scribed by Daniel A. Adsmond; David J. W. Grant


Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
448 KB
Volume
90
Category
Article
ISSN
0022-3549

No coin nor oath required. For personal study only.

โœฆ Synopsis


The hydrogen-bond connectivity in 39 sulfonamide crystal structures has been deciphered and described using graph set notation. The hydrogen-bond connectivity observed is used to gain information on hydrogen-bond preferences of speciยฎc donor and acceptor atoms of related sulfonamide molecules. The amido protons show a greater preference for hydrogen bonding to amidine nitrogens and cocrystal guests, whereas the amino protons show a greater preference for hydrogen bonding to sulfonyl oxygens, forming the only dominant hydrogen-bond pattern, a chain with an eight atom repeat unit. Preferential hydrogen bonding between the amidine group and the guest carboxyl group was observed in ยฎve cocrystal structures of sulfamethazine. Sulfamoxole displays a conformation and a hydrogen-bond motif not seen in any other structures. Sulfamerazine and sulfamethazine, differing by a methyl group, show no similarity in hydrogen-bond pattern, whereas sulfamethoxydiazine and sulfamethoxymethazine, which have sterically similar but chemically different heterocycles, show a striking similarity in hydrogen-bond pattern. Sulfamethoxydiazine, sulfamethoxymethazine, and sulfamethoxazole also show a large variation in hydrogen-bond pattern between polymorphs. Studies such as this, by revealing details of hydrogen-bonding patterns in closely related organic crystal structures, can potentially provide predictive capability among the crystal structures of pharmaceutical solids.


๐Ÿ“œ SIMILAR VOLUMES


Hydrogen bonding in nitrocellulose
โœ B. W. Brodman; M. P. Devine ๐Ÿ“‚ Article ๐Ÿ“… 1980 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 137 KB ๐Ÿ‘ 1 views
Hydrogen bonding in Alcohols
โœ Neil S. Berman ๐Ÿ“‚ Article ๐Ÿ“… 1968 ๐Ÿ› American Institute of Chemical Engineers ๐ŸŒ English โš– 272 KB ๐Ÿ‘ 1 views
Hydrogen bonding in MM2
โœ Norman L. Allinger; Randall A. Kok; Mita R. Imam ๐Ÿ“‚ Article ๐Ÿ“… 1988 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 496 KB

Hydrogen bonding is qualitatively accounted for in the early versions of the MM2 program, but not quantitatively. Experimentally, the hydrogen bonds are somewhat shorter and stronger than calculated by MM2. This has been corrected now in MM2(87), by reducing the van der Waals radius of the hydrogen

On hydrogen bonding in amylose
โœ W. Banks; C. T. Greenwood ๐Ÿ“‚ Article ๐Ÿ“… 1972 ๐Ÿ› Wiley (John Wiley & Sons) ๐ŸŒ English โš– 304 KB ๐Ÿ‘ 1 views