ORGLIST: Acetonitrile pKa

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From: Jim Sims (jsims$##$ucrac1.ucr.edu)
Date: Mon Mar 19 2001 - 12:28:19 EST


Cram's carbanion book lists the pKa of acetonitrile, malononitrile, and
cyanoform respectively as 25, 12, and 0. Reference quoted: JACS, 75, 2439
(1953).






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>Greetings! The pKa of acetonitrile is known to be 24; deprotonation occurs
>easily with strong bases or alkali metals. The pKa of Cyanoform was
>measured back in the 50's at Dupont, to be -5 (yes, minus 5!) in either
>H2SO4 or HClO4. A pKa value of 11.2 appears to be too high for
>malononitrile; it could be around 4-6.
>
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Professor Jim Sims
Department of Plant Pathology
University of California, Riverside
Riverside, CA 92521
Voice: 909 787 4127
FAX 909 787 4294


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