Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion

S. W. Ng; P. Naumov; M. G.B. Drew; G. Wojciechowski; B. Brzezinski

doi:10.1016/S0022-2860(01)00489-6

Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion

S. W. Ng, P. Naumov, M. G.B. Drew, G. Wojciechowski, B. Brzezinski

Chemistry

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

Abstract

In the reaction between 3,5-dinitrosalicylic acid and urotropine, the proton of the phenolic group is transferred to a nitrogen atom of urotropine to form a hydrogen-bonded ion-paired [N⋯O_phenolate = 2.777(4) A˚] compound. An analogous reaction between the acid and dicyclohexylamine yields a centrosymmetric ion-paired dimer [N⋯O_phenolate = 2.864(4), N⋯O_carbonyl = 2.940(5) A˚]. The structures of the two compounds are discussed in relation to their infrared spectral features. The structure of the anion is also investigated theoretically by geometry-optimization calculations.

Original language	English (US)
Pages (from-to)	29-37
Number of pages	9
Journal	Journal of Molecular Structure
Volume	595
Issue number	1-3
DOIs	https://doi.org/10.1016/S0022-2860(01)00489-6
State	Published - Sep 12 2001

Keywords

3,5-Dinitrosalicylic acid
Crystal structure
Dicyclohexylamine
FT-IR spectroscopy
Hydrogen bonds
NMR spectroscopy
Proton polarizability
Theoretical calculations
Urotropine

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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10.1016/S0022-2860(01)00489-6

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@article{a1c9b352923442f6b80b8bec60388715,

title = "Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion",

abstract = "In the reaction between 3,5-dinitrosalicylic acid and urotropine, the proton of the phenolic group is transferred to a nitrogen atom of urotropine to form a hydrogen-bonded ion-paired [N⋯Ophenolate = 2.777(4) A˚] compound. An analogous reaction between the acid and dicyclohexylamine yields a centrosymmetric ion-paired dimer [N⋯Ophenolate = 2.864(4), N⋯Ocarbonyl = 2.940(5) A˚]. The structures of the two compounds are discussed in relation to their infrared spectral features. The structure of the anion is also investigated theoretically by geometry-optimization calculations.",

keywords = "3,5-Dinitrosalicylic acid, Crystal structure, Dicyclohexylamine, FT-IR spectroscopy, Hydrogen bonds, NMR spectroscopy, Proton polarizability, Theoretical calculations, Urotropine",

author = "Ng, {S. W.} and P. Naumov and Drew, {M. G.B.} and G. Wojciechowski and B. Brzezinski",

year = "2001",

month = sep,

day = "12",

doi = "10.1016/S0022-2860(01)00489-6",

language = "English (US)",

volume = "595",

pages = "29--37",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

number = "1-3",

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TY - JOUR

T1 - Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion

AU - Ng, S. W.

AU - Naumov, P.

AU - Drew, M. G.B.

AU - Wojciechowski, G.

AU - Brzezinski, B.

PY - 2001/9/12

Y1 - 2001/9/12

N2 - In the reaction between 3,5-dinitrosalicylic acid and urotropine, the proton of the phenolic group is transferred to a nitrogen atom of urotropine to form a hydrogen-bonded ion-paired [N⋯Ophenolate = 2.777(4) A˚] compound. An analogous reaction between the acid and dicyclohexylamine yields a centrosymmetric ion-paired dimer [N⋯Ophenolate = 2.864(4), N⋯Ocarbonyl = 2.940(5) A˚]. The structures of the two compounds are discussed in relation to their infrared spectral features. The structure of the anion is also investigated theoretically by geometry-optimization calculations.

AB - In the reaction between 3,5-dinitrosalicylic acid and urotropine, the proton of the phenolic group is transferred to a nitrogen atom of urotropine to form a hydrogen-bonded ion-paired [N⋯Ophenolate = 2.777(4) A˚] compound. An analogous reaction between the acid and dicyclohexylamine yields a centrosymmetric ion-paired dimer [N⋯Ophenolate = 2.864(4), N⋯Ocarbonyl = 2.940(5) A˚]. The structures of the two compounds are discussed in relation to their infrared spectral features. The structure of the anion is also investigated theoretically by geometry-optimization calculations.

KW - 3,5-Dinitrosalicylic acid

KW - Crystal structure

KW - Dicyclohexylamine

KW - FT-IR spectroscopy

KW - Hydrogen bonds

KW - NMR spectroscopy

KW - Proton polarizability

KW - Theoretical calculations

KW - Urotropine

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U2 - 10.1016/S0022-2860(01)00489-6

DO - 10.1016/S0022-2860(01)00489-6

M3 - Article

AN - SCOPUS:0008735997

SN - 0022-2860

VL - 595

SP - 29

EP - 37

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

IS - 1-3

ER -

Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion

Abstract

Keywords

ASJC Scopus subject areas

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