Structure of 6-hydroxy-1-methylquinolinium chloride hydrate studied by X-ray, DFT calculations, FTIR and NMR spectroscopes

被引：5

作者：

Barczynski, P. ^{[1
]}

Komasa, A. ^{[1
]}

Ratajczak-Sitarz, M. ^{[1
]}

Katrusiak, A. ^{[1
]}

Koput, J. ^{[1
]}

Dega-Szafran, Z. ^{[1
]}

Szafran, M. ^{[1
]}

机构：

[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2010年 / 984卷 / 1-3期

关键词：

6-Hydroxy-1-methylquinolinium chloride; X-ray diffraction; FTIR and NMR spectra; DFT calculations; Hydrogen bonds; HETEROAROMATIC HYDROXY-COMPOUNDS; VIBRATIONAL-SPECTRA; AB-INITIO; MOLECULAR-STRUCTURE; CHEMICAL-SHIFTS; SCALING FACTORS; PROTON; CONFORMATION; TAUTOMERISM; DIFFRACTION;

D O I：

10.1016/j.molstruc.2010.10.007

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The crystal structure of 6-hydroxy-1-methylquinolinium chloride hydrate (1), 6QBWHCl, is monoclinic, space group P2(1)/n and Z = 4. 1-Methyl-6-oxyquinolinium betaine, 6QB, is protonated and its OH group participates in a moderate hydrogen bond with water molecule (O(1)-H center dot center dot center dot O(W1)= 2.636(2) angstrom). The water molecule is further connected by a hydrogen bond to chloride ion (O(W1)-H(W2)center dot center dot center dot Cl(1)= 3.090(3) angstrom). Structures of five complexes (2-6) have been optimized by the B3LYP/6-311G(d, p) level of theory and the results have been compared with the X-ray data of 1. Linear correlations between the experimental H-1 and C-13 NMR chemical shifts (delta(exp)) of complexes 2-5 and the magnetic isotropic shielding constants (sigma(cal)) calculated by the GIAO/B3LYP/6-311G(d, p) approach, using the screening solvation model (COSMO), delta(exp) = a + b sigma(cal), are reported. The probable assignments of the anharmonic experimental solid state vibrational frequencies of anhydrous complex, 6QBHCl, based on the calculated B3LYP/6-311G(d, p) harmonic frequencies have been proposed. (C) 2010 Elsevier B.V. All rights reserved.

引用

收藏

页码：359 / 370

页数：12

相关论文

共 50 条

[11] Structure of 2,3-dicarboxy-1-methylpyridinium chloride studied by X-ray diffraction, DFT calculation, NMR, FTIR and Raman spectra [J].

Barczynski, P. ;

Szafran, M. ;

Ratajczak-Sitarz, M. ;

Nowaczyk, L. ;

Dega-Szafran, Z. ;

Katrusiak, A. .

JOURNAL OF MOLECULAR STRUCTURE, 2012, 1018 :21-27

[12] Molecular structure of quinuclidine betaine hydrate studied by X-ray diffraction, DFT, FTIR, Raman, NMR methods [J].

Dega-Szafran, Z. ;

Katrusiak, A. ;

Szafran, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2009, 921 (1-3) :295-299

[13] Hydrogen bonding and molecular association in 2-(quinuclidinium)-butyric acid bromide hydrate studied by X-ray diffraction, DFT calculations, FTIR and NMR spectroscopy, and potentiometric titration [J].

Dega-Szafran, Z. ;

Katrusiak, A. ;

Szafran, M. ;

Barczynski, P. .

JOURNAL OF MOLECULAR STRUCTURE, 2010, 975 (1-3) :357-366

[14] Structure of 1-carboxymethylpyridinium-4-carboxylate inner salt studied by X-ray diffraction, DFT calculations, vibrational and NMR spectra [J].

Barczynski, P. ;

Katrusiak, A. ;

Koput, J. ;

Dega-Szafran, Z. ;

Szafran, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2009, 933 (1-3) :20-29

[15] Chalcogen analogues of nicotine lactam studied by NMR, FTIR, DFT and X-ray methods [J].

Jasiewicz, Beata ;

Malczewska-Jaskola, Karolina ;

Kowalczyk, Iwona ;

Warzajtis, Beata ;

Rychlewska, Urszula .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 128 :773-780

[16] Structure and conformation of 2,3-diethoxycarbonyl-1-methylpyridinium iodide studied by NMR, FTIR, Raman, X-ray diffraction and DFT methods [J].

Barczynski, P. ;

Ratajczak-Sitarz, M. ;

Nowaczyk, L. ;

Katrusiak, A. ;

Dega-Szafran, Z. ;

Komasa, A. ;

Szafran, M. .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 115 :208-218

[17] Orientations of water molecule and hydronium ion in 1-methylquinolinium-3-carboxy chloride monohydrate studied by X-ray diffraction, DFF calculations, NMR, FTIR and Raman spectra [J].

Barczynski, P. ;

Katrusiak, A. ;

Koput, J. ;

Dega-Szafran, Z. ;

Szafran, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2009, 918 (1-3) :39-54

[18] Crystal and molecular structure of quinuclidine betaine hydrochloride studied by X-ray diffraction, DFT, FTIR, and NMR methods [J].

Dega-Szafran, Z. ;

Katrusiak, A. ;

Szafran, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2009, 929 (1-3) :182-186

[19] Ring inversion in 4-hydroxy-1-methylpiperidine betaine studied by X-ray, FTIR, 13C CP MAS NMR and DFT calculations [J].

Dega-Szafran, Z. ;

Dutkiewicz, G. ;

Fojud, Z. ;

Kosturkiewicz, Z. ;

Szafran, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2009, 917 (2-3) :76-83

[20] Structure of 1H-2-oxo-2,3-dihydroimidazo[1,2-a]pyridinium perchlorate studied by X-ray diffraction, DFT calculations and by FTIR and NMR spectroscopy [J].

Kowalczyk, I. ;

Bartoszak-Adamska, E. ;

Jaskolski, M. ;

Dega-Szafran, Z. ;

Szafran, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2010, 976 (1-3) :119-128

← 1 2 3 4 5 →