The structure of 4,5,6,7-tetrafluoro-1H-benzotriazole in solid state and in solution

被引:0
作者
Santa Maria, Dolores [1 ]
Claramunt, Rosa M. [1 ]
Alkorta, Ibon [2 ]
Elguero, Jose
Javier Zuniga, Fco. [3 ]
机构
[1] Univ Nacl Educ Distancia, Fac Ciencias, Dept Quim Organ & Bioorgan, Senda Rey 4, E-28040 Madrid, Spain
[2] CSIC, Ctr Quim Organ Lora Tamayo, Inst Quim Med, Juan Cierva 3, Madrid 28006, Spain
[3] Univ Basque Country, Fac Ciencias & Tecnol, Dept Fis Mat Condensada, Apdo 644, E-48080 Bilbao, Spain
关键词
Benzotriazole; Tautomerism; F-19; NMR; X-ray diffraction analysis; DFT calculations; CENTER-DOT-F; INTERMOLECULAR INTERACTIONS; MOLECULAR-STRUCTURES; NMR-SPECTROSCOPY; CHEMICAL-SHIFTS; TAUTOMERISM; HALOGEN; BENZOTRIAZOLE; PYRAZOLES; C-13;
D O I
10.1016/j.jfluchem.2016.10.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This work reports the behavior in solution and in the solid-state of the title compound, a known but neglected benzotriazole. In solution, we have measured the prototropic barrier corresponding to the N1H/N3H tautomerism. In the solid-state, we have determined the X-ray molecular structure and the NMR chemical shifts. For both states and both properties (geometry and chemical shifts), theoretical calculations at the B3LYP/6-311++G(d,p) level proved invaluable. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:98 / 104
页数:7
相关论文
共 57 条
[1]   Barriers to the intramolecular N- to N-transfer of different groups in pyrazoles: Prototropy vs. elementotropy [J].
Alkorta, I ;
Elguero, J .
HETEROATOM CHEMISTRY, 2005, 16 (07) :628-636
[2]   A computational approach to intermolecular proton transfer in the solid state: assistance by proton acceptor molecules [J].
Alkorta, I ;
Rozas, I ;
Elguero, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (12) :2671-2675
[3]   1,2-proton shifts in pyrazole and related systems: a computational study of [1,5]-sigmatropic migrations of hydrogen and related phenomena [J].
Alkorta, I ;
Elguero, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (11) :2497-2503
[4]   Proton transfer in C-halogen pyrazole cyclamers.: A theoretical study [J].
Alkorta, Ibon ;
Blanco, Fernando ;
Elguero, Jose .
STRUCTURAL CHEMISTRY, 2008, 19 (02) :191-198
[5]   The annular tautomerism of imidazoles and pyrazoles: The possible existence of nonaromatic forms [J].
Alkorta, Ibon ;
Elguero, Jose ;
Liebman, Joel F. .
STRUCTURAL CHEMISTRY, 2006, 17 (04) :439-444
[6]   A theoretical and experimental study of the NMR spectra of 4,5,6,7-tetrafluorobenzazoles with special stress on PCM calculations of chemical shifts [J].
Alkorta, Ibon ;
Elguero, Jose ;
Perez-Torralba, Marta ;
Lopez, Concepcion ;
Claramunt, Rosa M. .
MAGNETIC RESONANCE IN CHEMISTRY, 2015, 53 (05) :353-362
[7]   A theoretical study of the parent NH-benzazoles (benzimidazoles, indazoles and benzotriazoles): geometries, energies, acidity and basicity, NMR properties and molecular electrostatic potentials [J].
Alkorta, Ibon ;
Sanchez-Sanz, Goar ;
Trujillo, Cristina ;
Elguero, Jose ;
Claramunt, Rosa M. .
ARKIVOC, 2012, :85-106
[8]   Functionalization of Non-activated C?H Bonds of Alkanes: An Effective and Recyclable Catalytic System Based on Fluorinated Silver Catalysts and Solvents [J].
Angeles Fuentes, M. ;
Munoz, Bianca K. ;
Jacob, Kane ;
Vendier, Laure ;
Caballero, Ana ;
Etienne, Michel ;
Perez, Pedro J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (04) :1327-1334
[9]  
[Anonymous], 2016, WEB SCI WEB KNOWL
[10]   The nature of halogen ... halogen synthons: Crystallographic and theoretical studies [J].
Awwadi, Firas F. ;
Willett, Roger D. ;
Peterson, Kirk A. ;
Twamley, Brendan .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (35) :8952-8960