Universität zu Köln

Gumbert, Silke D., Koerbitzer, Meike, Alig, Edith, Schmidt, Martin U., Chierotti, Michele R. ORCID: 0000-0002-8734-6009, Gobetto, Roberto, Li, Xiaozhou ORCID: 0000-0003-3882-7073 and van de Streek, Jacco ORCID: 0000-0002-3026-4213 (2016). Crystal structure and tautomerism of Pigment Yellow 138 determined by X-ray powder diffraction and solid-state NMR. Dyes Pigment., 131. S. 364 - 373. OXFORD: ELSEVIER SCI LTD. ISSN 1873-3743

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Abstract

The crystal structure of C.I. Pigment Yellow 138 was determined from X-ray powder diffraction data using real-space methods with subsequent Rietveld refinements. The tautomeric state was investigated by solid-state 1D and 2D multinuclear NMR experiments. In the crystals, the compound exhibits the NH-tautomer with a hydrogen atom situated at the nitrogen of the quinoline moiety. Direct evidence of the presence of the NH-tautomer is provided by H-1-N-14 HMQC solid-state NMR at very fast MAS. Solid-state dispersion-corrected density functional theory calculations with BLYP-D3 confirm the correctness of the crystal structure and support the N-H tautomer. The NH hydrogen atom forms an intramolecular resonance-assisted N-H center dot center dot center dot O hydrogen bond to the neighbouring indandione moiety. The indandione moiety is almost coplanar with the quinoline fragment, whereas the phthalimide group forms an angle of 57 with it. Quantum-mechanical calculations show that for an isolated molecule this tautomeric form is by approximately 60 kJ/lmol more stable than the OH-form with a hydrogen atom placed at an oxygen atom of the indandione moiety. The out-of plane rotation of the phthalimide group is not a packing effect, but caused by intramolecular steric hindrance. (C) 2016 Published by Elsevier Ltd.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Gumbert, Silke D. UNSPECIFIED UNSPECIFIED UNSPECIFIED Koerbitzer, Meike UNSPECIFIED UNSPECIFIED UNSPECIFIED Alig, Edith UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmidt, Martin U. UNSPECIFIED UNSPECIFIED UNSPECIFIED Chierotti, Michele R. UNSPECIFIED orcid.org/0000-0002-8734-6009 UNSPECIFIED Gobetto, Roberto UNSPECIFIED UNSPECIFIED UNSPECIFIED Li, Xiaozhou UNSPECIFIED orcid.org/0000-0003-3882-7073 UNSPECIFIED van de Streek, Jacco UNSPECIFIED orcid.org/0000-0002-3026-4213 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-268749
DOI:	10.1016/j.dyepig.2016.03.035
Journal or Publication Title:	Dyes Pigment.
Volume:	131
Page Range:	S. 364 - 373
Date:	2016
Publisher:	ELSEVIER SCI LTD
Place of Publication:	OXFORD
ISSN:	1873-3743
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language TOTAL-ENERGY CALCULATIONS; CPMAS NMR; RESONANCE; SPECTROSCOPY; POLYMORPHISM; COLLECTION; DESMOTROPY; COMPLEXES; PHASE; FIELD Multiple languages Chemistry, Applied; Engineering, Chemical; Materials Science, Textiles Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/26874