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Herein we report that cyanohydrins, generated by the reaction of cyanide with \u03b2\u2010keto acids and \u03b3\u2010keto\u2010alcohols, spontaneously hydrolyze under ambient conditions (aqueous medium, RT, and a range of pH). The spontaneous hydrolysis is affected by an intramolecular proton transfer and an intramolecular 5\u2010<jats:italic>exo<\/jats:italic>\u2010dig attack, but with a twist. In the case of \u03b2\u2010keto acids, the hydrolysis is mediated by the neighboring carboxylic acid group only at pH values less than 7, whereas in the case of \u03b3\u2010keto\u2010alcohols the hydrolysis is mediated by the neighboring hydroxyl group only at pH values greater than 7. The results, in combination with previous works, have implications for selective transformations of cyanide\u2010initiated prebiotic systems chemistry.<\/jats:p>","DOI":"10.1002\/chem.201701497","type":"journal-article","created":{"date-parts":[[2017,5,4]],"date-time":"2017-05-04T22:22:57Z","timestamp":1493936577000},"page":"8756-8765","source":"Crossref","is-referenced-by-count":15,"title":["Anchimeric\u2010Assisted Spontaneous Hydrolysis of Cyanohydrins Under Ambient Conditions: Implications for Cyanide\u2010Initiated Selective Transformations"],"prefix":"10.1002","volume":"23","author":[{"given":"Jayasudhan Reddy","family":"Yerabolu","sequence":"first","affiliation":[{"name":"Department of Chemistry The Scripps Research Institute  10550 North Torrey Pines Rd La Jolla CA 92037 USA"},{"name":"NSF-NASA Center for Chemical Evolution  Atlanta GA 30332 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Charles 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