Controlling Disulfide Bond Formation and Crystal Growth from 2-Mercaptobenzoic Acid

• Published in: Crystal growth & design Vol. 11; no. 4; pp. 1370 - 1374
• Main Authors: Rowland, Clare E, Cantos, Paula M, Toby, Brian H, Frisch, Mark, Deschamps, Jeffrey R, Cahill, Christopher L
• Format: Journal Article
• Language: English
• Published: Washington,DC American Chemical Society 06.04.2011
• Subjects: Condensed matter: structure, mechanical and thermal properties; Cross-disciplinary physics: materials science; rheology; Exact sciences and technology; Liquid crystals; materials and chemistry by design; MATERIALS SCIENCE; Methods of crystal growth; physics of crystal growth; nuclear (including radiation effects); Physics; Structure of solids and liquids; crystallography; synthesis (novel materials); synthesis (self-assembly); Crystal growth; pH value; Hydrothermal synthesis; Thiols; Cocrystal; Benzenic compound; pH effect; Oxidation; Neutral solution; Liquid crystals
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/cg101619y

We report disulfide bond formation from 2-mercaptobenzoic acid (2-MBA) under hydrothermal conditions as a function of pH. Under acidic conditions, 2-MBA remains unchanged. Upon increasing pH, however, we observe 50% oxidation to 2,2′-disulfanediyldibenzoic acid (2,2′-DSBA), which is isolated as a cocrystal of both the thiol and disulfide molecules. At neutral pH, we observe complete oxidation and concurrent crystal growth. The pH sensitivity of this system allows targeting crystals of specific composition from simple building units through a straightforward pH manipulation.