concerted solvent processes for common sulfonyl chloride precursors used in the synthesis of sulfonamide-based drugs共同溶剂过程中常用的磺酰氯前体的合成sulfonamide-based药物.pdf

Int. J. Mol. Sci. 2008, 9, 914-925; DOI: 10.3390/ijms9050914 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 /ijms Article Concerted Solvent Processes for Common Sulfonyl Chloride Precursors used in the Synthesis of Sulfonamide-based Drugs Malcolm J. D’Souza 1,*, Lamia Yaakoubd 1, Stacey L. Mlynarski 1, and Dennis N. Kevill 2,* 1 Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA; E-mail: DSouzaMa@W 2 Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115- 2862, USA; E-mail: dkevill@ * Authors to whom correspondence should be addressed. Received: 9 April 2008; in revised form: 19 May 2008 / Accepted: 19 May 2008 / Published: 24 May 2008 Abstract: Specific rates of solvolysis in hydroxylic solvents available for the solvolysis of 2-thiophenesulfonyl chloride and phenylmethanesulfonyl chloride are supplemented by determining the values in fluoroalcohol-containing solvents. The data sets are then correlated using the extended Grunwald-Winstein equation. For both substrates, it is found that a single correlation controls the influence of solvent over the full range of solvent composition. The sensitivities to solvent nucleophilicity and solvent ionizing power are compared to values available for other substrates. Three of these previ