The crystal structures of three azonaphtharylamide pigments

Chia Hsien Chang; Robert M. Christie; Georgina M. Rosair

doi:10.1016/j.dyepig.2008.12.007

The crystal structures of three azonaphtharylamide pigments

Chia Hsien Chang, Robert M. Christie, Georgina M. Rosair

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

8 Citations (Scopus)

Abstract

The single crystal X-ray structures of three structurally related azonaphtharylamide pigments are reported. Two azo pigments derived from 4-amino-3-nitrotoluene as diazo component (1a and b) crystallize in the centrosymmetric space group P2₁/c while the third (1c), an analogue of 1b but derived from 2,5-dichloroaniline as diazo component, crystallizes in the chiral space group P2₁2₁2₁. The compounds adopt the ketohydrazone tautomeric forms with intramolecular, but no intermolecular, hydrogen bonding. The application performance of the products is discussed in relation to the molecular and crystal structures. X-ray powder diffraction, supported by FTIR spectroscopic and DSC analysis, demonstrate that pigment 1a shows polymorphism. The application performances of the two polymorphs of this pigment are compared. © 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	147-155
Number of pages	9
Journal	Dyes and Pigments
Volume	82
Issue number	2
DOIs	https://doi.org/10.1016/j.dyepig.2008.12.007
Publication status	Published - Aug 2009

Keywords

Azonaphtharylamide
Pigments
Polymorphism
X-ray single crystal structure

Access to Document

10.1016/j.dyepig.2008.12.007

Cite this

@article{d30b0e1b4f794de087fb2cd0961b75df,

title = "The crystal structures of three azonaphtharylamide pigments",

abstract = "The single crystal X-ray structures of three structurally related azonaphtharylamide pigments are reported. Two azo pigments derived from 4-amino-3-nitrotoluene as diazo component (1a and b) crystallize in the centrosymmetric space group P21/c while the third (1c), an analogue of 1b but derived from 2,5-dichloroaniline as diazo component, crystallizes in the chiral space group P212121. The compounds adopt the ketohydrazone tautomeric forms with intramolecular, but no intermolecular, hydrogen bonding. The application performance of the products is discussed in relation to the molecular and crystal structures. X-ray powder diffraction, supported by FTIR spectroscopic and DSC analysis, demonstrate that pigment 1a shows polymorphism. The application performances of the two polymorphs of this pigment are compared. {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

keywords = "Azonaphtharylamide, Pigments, Polymorphism, X-ray single crystal structure",

author = "Chang, {Chia Hsien} and Christie, {Robert M.} and Rosair, {Georgina M.}",

year = "2009",

month = aug,

doi = "10.1016/j.dyepig.2008.12.007",

language = "English",

volume = "82",

pages = "147--155",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier",

number = "2",

}

TY - JOUR

T1 - The crystal structures of three azonaphtharylamide pigments

AU - Chang, Chia Hsien

AU - Christie, Robert M.

AU - Rosair, Georgina M.

PY - 2009/8

Y1 - 2009/8

N2 - The single crystal X-ray structures of three structurally related azonaphtharylamide pigments are reported. Two azo pigments derived from 4-amino-3-nitrotoluene as diazo component (1a and b) crystallize in the centrosymmetric space group P21/c while the third (1c), an analogue of 1b but derived from 2,5-dichloroaniline as diazo component, crystallizes in the chiral space group P212121. The compounds adopt the ketohydrazone tautomeric forms with intramolecular, but no intermolecular, hydrogen bonding. The application performance of the products is discussed in relation to the molecular and crystal structures. X-ray powder diffraction, supported by FTIR spectroscopic and DSC analysis, demonstrate that pigment 1a shows polymorphism. The application performances of the two polymorphs of this pigment are compared. © 2009 Elsevier Ltd. All rights reserved.

AB - The single crystal X-ray structures of three structurally related azonaphtharylamide pigments are reported. Two azo pigments derived from 4-amino-3-nitrotoluene as diazo component (1a and b) crystallize in the centrosymmetric space group P21/c while the third (1c), an analogue of 1b but derived from 2,5-dichloroaniline as diazo component, crystallizes in the chiral space group P212121. The compounds adopt the ketohydrazone tautomeric forms with intramolecular, but no intermolecular, hydrogen bonding. The application performance of the products is discussed in relation to the molecular and crystal structures. X-ray powder diffraction, supported by FTIR spectroscopic and DSC analysis, demonstrate that pigment 1a shows polymorphism. The application performances of the two polymorphs of this pigment are compared. © 2009 Elsevier Ltd. All rights reserved.

KW - Azonaphtharylamide

KW - Pigments

KW - Polymorphism

KW - X-ray single crystal structure

UR - http://www.scopus.com/inward/record.url?scp=62549166191&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2008.12.007

DO - 10.1016/j.dyepig.2008.12.007

M3 - Article

SN - 0143-7208

VL - 82

SP - 147

EP - 155

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 2

ER -

The crystal structures of three azonaphtharylamide pigments

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this