Examinations of Dimethyl Sulfoxide-Phase Equilibrium Acidities of Selected Polycyclic Aromatic Compounds

Autor:	B. M. Peterson, G. Jirka, Mark J. Bausch, D. Selmarten, C. Guadalupe-Fasano
Rok vydání:	1991
Předmět:	Steric effects Polymers and Plastics Phase equilibrium Chemistry Stereochemistry Dimethyl sulfoxide Organic Chemistry Resonance (chemistry) chemistry.chemical_compound Phenalene Materials Chemistry Moiety Cross-conjugation Carbanion
Zdroj:	Polycyclic Aromatic Compounds. 2:19-27
ISSN:	1563-5333 1040-6638
DOI:	10.1080/10406639108047854
Popis:	Comparisons of dimethyl sulibxide (DMSO)-phase pK a's (in parentheses) for 10-cyano-9-methoxymethy-lanthracene (17.35), 10-cyano-9-phenoxymethylanthracene (14.9), 9-cyanomethoxymethylanthracene (20.4), and (α-methoxy) phenylacetonitrile (23.0) with literature DMSO-phase pK a's for 9-methylanth-racene, 9-methoxymethylanthracene, 9-phenoxymethylanthracene, 9-cyanomethylanthracene, 10-cyano-9-methylanthracene, and phenylacetonitrile (31.1, 30.6, 30.2, 19.7, 20.0, and 21.9, respectively), indicate that: (a) α-methoxy and α-phenoxy substituents acidify 10-cyano-9-methylanthracene; (b) an α-methoxy moiety deacidifies 9-cyanomethylanthracene and phenylacetonitrile; and (c) 10-cyano substituents acidify 9-methylanthracene, 9-methoxymethylanthracene, and 9-phenoxymethylanthracene by 11.1, 13.25, and 15.3 pK a units, respectively. These data are indicative of steric inhibition of resonance, resonance saturation, and effects due to cross conjugation, in carbanions derived from variously substituted 9-methyl...
Databáze:	OpenAIRE
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