Structural, spectroscopic and theoretical studies of the 2:2 complex of 5,5′-dibromo-2,2′-biphenol with 1,5,7-triazabicyclo[4.4.0]dec-5-ene

G. Wojciechowski; B. Brzezinski; P. Naumov; S. Chantrapromma; A. R. Ibrahim; H. K. Fun; S. W. Ng

doi:10.1016/S0022-2860(01)00589-0

Structural, spectroscopic and theoretical studies of the 2:2 complex of 5,5′-dibromo-2,2′-biphenol with 1,5,7-triazabicyclo[4.4.0]dec-5-ene

G. Wojciechowski, B. Brzezinski, P. Naumov, S. Chantrapromma, A. R. Ibrahim, H. K. Fun, S. W. Ng

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 5,5′-dibromo-2,2′-biphenol a cooperative inter-intra-molecular hydrogen-bonded system is formed. The intermolecular hydrogen bonds are relatively long [2.708(6) and 2.895(7)] and do not show large proton polarizability. The intramolecular OHO^- hydrogen bond is relatively short [2.489(6)]. The structure of the complex is very well reflected in its FT-IR spectrum in the solid. On the basis of the FT-IR and ¹H NMR studies of the complex in chloroform and in acetonitrile a structure different than in the solid is proposed. DFT structures of both isolated ions in their ground electronic states at the B3LYP/6-31 + +G(d,p) level are employed to follow the effects of the hydrogen bonding on the intrinsic ionic structures.

Original language	English (US)
Pages (from-to)	153-159
Number of pages	7
Journal	Journal of Molecular Structure
Volume	598
Issue number	2-3
DOIs	https://doi.org/10.1016/S0022-2860(01)00589-0
State	Published - 2001

Keywords

1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)
5,5′-Dibromo-2,2′-biphenol
Ab initio calculations
Crystal structure
FT-IR spectroscopy
H NMR spectroscopy
Hydrogen bond
Strong N-base

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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10.1016/S0022-2860(01)00589-0

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@article{f7034d116a23423392438656008d32b5,

title = "Structural, spectroscopic and theoretical studies of the 2:2 complex of 5,5′-dibromo-2,2′-biphenol with 1,5,7-triazabicyclo[4.4.0]dec-5-ene",

abstract = "In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 5,5′-dibromo-2,2′-biphenol a cooperative inter-intra-molecular hydrogen-bonded system is formed. The intermolecular hydrogen bonds are relatively long [2.708(6) and 2.895(7)] and do not show large proton polarizability. The intramolecular OHO- hydrogen bond is relatively short [2.489(6)]. The structure of the complex is very well reflected in its FT-IR spectrum in the solid. On the basis of the FT-IR and 1H NMR studies of the complex in chloroform and in acetonitrile a structure different than in the solid is proposed. DFT structures of both isolated ions in their ground electronic states at the B3LYP/6-31 + +G(d,p) level are employed to follow the effects of the hydrogen bonding on the intrinsic ionic structures.",

keywords = "1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), 5,5′-Dibromo-2,2′-biphenol, Ab initio calculations, Crystal structure, FT-IR spectroscopy, H NMR spectroscopy, Hydrogen bond, Strong N-base",

author = "G. Wojciechowski and B. Brzezinski and P. Naumov and S. Chantrapromma and Ibrahim, {A. R.} and Fun, {H. K.} and Ng, {S. W.}",

note = "Funding Information: We thank Polish Committee for Scientific Research (KBN, Research Project 3 T09A 01817) and the National Science Council for R and D, Malaysia (IRPA 09-02-03-0662, 305/PFIZIK/610961) for supporting this work. The authors thank Prof. Yuji Ohashi from Tokyo Institute of Technology for kindly making the computer facilities available. P.N. acknowledges the Japanese Ministry for Science, Sports and Education (Monbusho) for the academic scholarship.",

year = "2001",

doi = "10.1016/S0022-2860(01)00589-0",

language = "English (US)",

volume = "598",

pages = "153--159",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier B.V.",

number = "2-3",

}

TY - JOUR

T1 - Structural, spectroscopic and theoretical studies of the 2:2 complex of 5,5′-dibromo-2,2′-biphenol with 1,5,7-triazabicyclo[4.4.0]dec-5-ene

AU - Wojciechowski, G.

AU - Brzezinski, B.

AU - Naumov, P.

AU - Chantrapromma, S.

AU - Ibrahim, A. R.

AU - Fun, H. K.

AU - Ng, S. W.

N1 - Funding Information: We thank Polish Committee for Scientific Research (KBN, Research Project 3 T09A 01817) and the National Science Council for R and D, Malaysia (IRPA 09-02-03-0662, 305/PFIZIK/610961) for supporting this work. The authors thank Prof. Yuji Ohashi from Tokyo Institute of Technology for kindly making the computer facilities available. P.N. acknowledges the Japanese Ministry for Science, Sports and Education (Monbusho) for the academic scholarship.

PY - 2001

Y1 - 2001

N2 - In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 5,5′-dibromo-2,2′-biphenol a cooperative inter-intra-molecular hydrogen-bonded system is formed. The intermolecular hydrogen bonds are relatively long [2.708(6) and 2.895(7)] and do not show large proton polarizability. The intramolecular OHO- hydrogen bond is relatively short [2.489(6)]. The structure of the complex is very well reflected in its FT-IR spectrum in the solid. On the basis of the FT-IR and 1H NMR studies of the complex in chloroform and in acetonitrile a structure different than in the solid is proposed. DFT structures of both isolated ions in their ground electronic states at the B3LYP/6-31 + +G(d,p) level are employed to follow the effects of the hydrogen bonding on the intrinsic ionic structures.

AB - In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 5,5′-dibromo-2,2′-biphenol a cooperative inter-intra-molecular hydrogen-bonded system is formed. The intermolecular hydrogen bonds are relatively long [2.708(6) and 2.895(7)] and do not show large proton polarizability. The intramolecular OHO- hydrogen bond is relatively short [2.489(6)]. The structure of the complex is very well reflected in its FT-IR spectrum in the solid. On the basis of the FT-IR and 1H NMR studies of the complex in chloroform and in acetonitrile a structure different than in the solid is proposed. DFT structures of both isolated ions in their ground electronic states at the B3LYP/6-31 + +G(d,p) level are employed to follow the effects of the hydrogen bonding on the intrinsic ionic structures.

KW - 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)

KW - 5,5′-Dibromo-2,2′-biphenol

KW - Ab initio calculations

KW - Crystal structure

KW - FT-IR spectroscopy

KW - H NMR spectroscopy

KW - Hydrogen bond

KW - Strong N-base

UR - http://www.scopus.com/inward/record.url?scp=0001761132&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001761132&partnerID=8YFLogxK

U2 - 10.1016/S0022-2860(01)00589-0

DO - 10.1016/S0022-2860(01)00589-0

M3 - Article

AN - SCOPUS:0001761132

SN - 0022-2860

VL - 598

SP - 153

EP - 159

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

IS - 2-3

ER -

Structural, spectroscopic and theoretical studies of the 2:2 complex of 5,5′-dibromo-2,2′-biphenol with 1,5,7-triazabicyclo[4.4.0]dec-5-ene

Abstract

Keywords

ASJC Scopus subject areas

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