Issue 9, 2001
From the journal:

New Journal of Chemistry

A short C–H···N hydrogen bond with a very strong IR spectroscopic effect

Stanisław Boryczka,a   Mark S. Rozenberg,b   Antoine M. M. Schreurs,c   Jan Kroon,c   Evgeni B. Starikovd  and  Thomas Steiner*d  

* Corresponding authors

a Department of Organic Chemistry, Silesian School of Medicine, 4 Jagiellonska Str., Sosnowiec, Poland

b Institute of Inorganic and Analytical Chemistry, The Hebrew Uniersity of Jerusalem, Jerusalem, Israel

c Bijoet Center for Biomolecular Research, Department of Crystal and Structural Chemistry, Utrecht Uniersity, Padualaan 8, Utrecht, The Netherlands

d Institut für Chemie—Kristallographie, Freie Uniersität Berlin, Takustraße 6, Berlin, Germany
E-mail: steiner@chemie.fu-berlin.de

Abstract

The crystal structure of 3-methylthio-4-propargylselenoquinoline contains a very short C[triple bond, length half m-dash]C–H···N hydrogen bond with H···N and C···N distances of 2.17 and 3.225(4) Å, respectively. The bathochromic shift of the infrared acetylenic C–H stretching vibration νCH is 176 cm−1. The geometry as well as the spectral effects come close to the shortest well-studied C–H···N hydrogen bond, which occurs in solid HCN (C···N = 3.18 Å, bathochromic shift 180 cm−1). The hydrogen bond energy is calculated as −3.4 kcal mol−1. A correlation of νCHbathochromic shift against C···N distance is established for C[triple bond, length half m-dash]C–H···N hydrogen bonds.

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Article information

DOI
https://doi.org/10.1039/B102727C
Article type
Letter
Submitted
23 Mar 2001
Accepted
08 Jun 2001
First published
09 Aug 2001

New J. Chem., 2001,25, 1111-1113

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A short C–H···N hydrogen bond with a very strong IR spectroscopic effect

S. Boryczka, M. S. Rozenberg, A. M. M. Schreurs, J. Kroon, E. B. Starikov and T. Steiner, New J. Chem., 2001, 25, 1111 DOI: 10.1039/B102727C

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