Structural, theoretical and spectroscopic studies of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene-4-nitrophenol

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

doi:10.1016/S0022-2860(00)00926-1

Structural, theoretical and spectroscopic studies of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene-4-nitrophenol

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

Chemistry

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

Abstract

In the crystal of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrophenol one hydrogen atom of the phenolic group is transferred to the TBD molecule and two NH protons form hydrogen bonds with one nitro group [N···O distances are 2.968(5), 2.985(4) Å]. This hydrogen-bonded segment is linked to another molecule of 4-nitrophenol by a short (O···H···O)^- hydrogen bond [O···O = 2.512(3)Å]. The structure of the cation is investigated theoretically by geometry-optimization calculations. The structure of the complex is very well reflected in its FTIR spectrum in the solid. The complex dissolution in acetonitrile causes its dissociation and its FTIR and ¹H NMR spectra prove the presence of the protonated TBD and (O···H···O)^- hydrogen-bonded 4-nitrophenol-4-nitrophenolate species. In chloroform a new structure of the complex is found and discussed.

Original language	English (US)
Pages (from-to)	185-196
Number of pages	12
Journal	Journal of Molecular Structure
Volume	562
Issue number	1-3
DOIs	https://doi.org/10.1016/S0022-2860(00)00926-1
State	Published - May 2 2001

Keywords

Crystal structure
FTIR spectroscopy
Intramolecular hydrogen bond
NMR spectroscopy
Strong N-base
TBD
Theoretical calculations

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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10.1016/S0022-2860(00)00926-1

Cite this

@article{44f3a3511b984306bcd0d2cb9b9c4f1a,

title = "Structural, theoretical and spectroscopic studies of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene-4-nitrophenol",

abstract = "In the crystal of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrophenol one hydrogen atom of the phenolic group is transferred to the TBD molecule and two NH protons form hydrogen bonds with one nitro group [N···O distances are 2.968(5), 2.985(4) {\AA}]. This hydrogen-bonded segment is linked to another molecule of 4-nitrophenol by a short (O···H···O)- hydrogen bond [O···O = 2.512(3){\AA}]. The structure of the cation is investigated theoretically by geometry-optimization calculations. The structure of the complex is very well reflected in its FTIR spectrum in the solid. The complex dissolution in acetonitrile causes its dissociation and its FTIR and 1H NMR spectra prove the presence of the protonated TBD and (O···H···O)- hydrogen-bonded 4-nitrophenol-4-nitrophenolate species. In chloroform a new structure of the complex is found and discussed.",

keywords = "Crystal structure, FTIR spectroscopy, Intramolecular hydrogen bond, NMR spectroscopy, Strong N-base, TBD, Theoretical calculations",

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

note = "Funding Information: We thank the National Science Council for R&D, Malaysia (IRPA 09-02-03-0662, 190-9609-2801), the Institute of Chemistry, {\textquoteleft}Sv. Kiril i Metodij{\textquoteright} University and Polish Committee for Scientific Research (KBN, Research Project 3 T09A 01817) for supporting this work. ",

year = "2001",

month = may,

day = "2",

doi = "10.1016/S0022-2860(00)00926-1",

language = "English (US)",

volume = "562",

pages = "185--196",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

number = "1-3",

}

TY - JOUR

T1 - Structural, theoretical and spectroscopic studies of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene-4-nitrophenol

AU - Ng, S. W.

AU - Naumov, P.

AU - Chantrapromma, S.

AU - Shanmuga Sundara Raj, S.

AU - Fun, H. K.

AU - Ibrahim, A. R.

AU - Wojciechowski, G.

AU - Brzezinski, B.

N1 - Funding Information: We thank the National Science Council for R&D, Malaysia (IRPA 09-02-03-0662, 190-9609-2801), the Institute of Chemistry, ‘Sv. Kiril i Metodij’ University and Polish Committee for Scientific Research (KBN, Research Project 3 T09A 01817) for supporting this work.

PY - 2001/5/2

Y1 - 2001/5/2

N2 - In the crystal of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrophenol one hydrogen atom of the phenolic group is transferred to the TBD molecule and two NH protons form hydrogen bonds with one nitro group [N···O distances are 2.968(5), 2.985(4) Å]. This hydrogen-bonded segment is linked to another molecule of 4-nitrophenol by a short (O···H···O)- hydrogen bond [O···O = 2.512(3)Å]. The structure of the cation is investigated theoretically by geometry-optimization calculations. The structure of the complex is very well reflected in its FTIR spectrum in the solid. The complex dissolution in acetonitrile causes its dissociation and its FTIR and 1H NMR spectra prove the presence of the protonated TBD and (O···H···O)- hydrogen-bonded 4-nitrophenol-4-nitrophenolate species. In chloroform a new structure of the complex is found and discussed.

AB - In the crystal of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrophenol one hydrogen atom of the phenolic group is transferred to the TBD molecule and two NH protons form hydrogen bonds with one nitro group [N···O distances are 2.968(5), 2.985(4) Å]. This hydrogen-bonded segment is linked to another molecule of 4-nitrophenol by a short (O···H···O)- hydrogen bond [O···O = 2.512(3)Å]. The structure of the cation is investigated theoretically by geometry-optimization calculations. The structure of the complex is very well reflected in its FTIR spectrum in the solid. The complex dissolution in acetonitrile causes its dissociation and its FTIR and 1H NMR spectra prove the presence of the protonated TBD and (O···H···O)- hydrogen-bonded 4-nitrophenol-4-nitrophenolate species. In chloroform a new structure of the complex is found and discussed.

KW - Crystal structure

KW - FTIR spectroscopy

KW - Intramolecular hydrogen bond

KW - NMR spectroscopy

KW - Strong N-base

KW - TBD

KW - Theoretical calculations

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U2 - 10.1016/S0022-2860(00)00926-1

DO - 10.1016/S0022-2860(00)00926-1

M3 - Article

AN - SCOPUS:0035795740

SN - 0022-2860

VL - 562

SP - 185

EP - 196

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

IS - 1-3

ER -

Structural, theoretical and spectroscopic studies of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene-4-nitrophenol

Abstract

Keywords

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