Stabilization of carboxylate anion with a NH... O hydrogen bond: Facilitation of the deprotonation of carboxylic acid by the neighboring amide NH groups

A Onoda, Y Yamada, J Takeda, Y Nakayama…

Index: Onoda, Akira; Yamada, Yusuke; Takeda, Jiro; Nakayama, Yoshiki; Okamura, Taka-Aki; Doi, Mototsugu; Yamamoto, Hitoshi; Ueyama, Norikazu Bulletin of the Chemical Society of Japan, 2004 , vol. 77, # 2 p. 321 - 329

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Citation Number: 25

Abstract

The formation of the NH··· O hydrogen bonds of carboxylic acids, 2, 6-(t-BuCONH) 2 C 6 H 3 COOH (1) and 2-t-BuCONH-6-MeC 6 H 3 COOH (2), carboxylate,[NEt 4][2, 6-(t-BuCONH) 2 C 6 H 3 COO](3), and a mixed complex,[N (n-Pr) 4][H {2, 6-(t-BuCONH) 2 C 6 H 3 (COO)} 2](4), were determined by X-ray structure analysis, 1 H NMR, and IR spectroscopy, both in the solid state and in solution. The amide NH group forms weak intramolecular hydrogen ...