Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Herein the nucleation pathway of conformational polymorphs was revealed by studying the relationships and distinctions among a series of α,ω-alkanedicarboxylic acids [HOOC–(CH2)n−2–COOH, named DAn, where n = 5, 7, 9, 11, 13, 15] in the solid state and in solution. Their polymorphic outcomes, with th...

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Main Authors:	Peng Shi, Shijie Xu, Yiming Ma, Weiwei Tang, Feng Zhang, Jingkang Wang, Junbo Gong
Format:	Article
Language:	English
Published:	International Union of Crystallography 2020-05-01
Series:	IUCrJ
Subjects:	conformational polymorphs nucleation routes α,ω-alkanedicarboxylic acids self-assembly conformational rearrangement intermolecular interactions polymorphism crystallization and crystal growth
Online Access:	http://scripts.iucr.org/cgi-bin/paper?S205225252000233X

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spelling	doaj-87ba4582d10749d4a69ff82d3de863122020-11-25T03:00:28ZengInternational Union of CrystallographyIUCrJ2052-25252020-05-017342243310.1107/S205225252000233Xlq5027Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acidsPeng Shi0Shijie Xu1Yiming Ma2Weiwei Tang3Feng Zhang4Jingkang Wang5Junbo Gong6School of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, People's Republic of ChinaTianjin Key Laboratory of Marine Resources and Chemistry, College of Chemical Engineering and Materials Science, Tianjin University of Science and Technology, Tianjin 300457, People's Republic of ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, People's Republic of ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, People's Republic of ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, People's Republic of ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, People's Republic of ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, People's Republic of ChinaHerein the nucleation pathway of conformational polymorphs was revealed by studying the relationships and distinctions among a series of α,ω-alkanedicarboxylic acids [HOOC–(CH2)n−2–COOH, named DAn, where n = 5, 7, 9, 11, 13, 15] in the solid state and in solution. Their polymorphic outcomes, with the exception of DA5, show solvent dependence: form I with conformation I crystallizes from solvents with hydrogen-bond donating (HBD) ability, whereas form II with conformation II crystallizes preferentially from solvents with no HBD ability. In contrast, form II of DA5 does not crystallize in any of the solvents used. Quantum mechanical computation showed that there is no direct conformational link between the solvents and the resultant polymorphic outcomes. Surprisingly, solute aggregates were found in no-HBD solvents by Fourier transform infrared spectroscopy, and only monomers could be detected in HBD solvents, suggesting stronger solvation. Furthermore, it was found that all six compounds including DA5 followed the same pattern in solution. Moreover, crystal-packing efficiency calculations and stability tests stated that dimorphs of DA5 bear a greater stability difference than others. These suggest that the rearrangement from conformation II to I could not be limited by hard desolvation in HBD solvents, where form I was also obtained. In other systems, metastable II was produced in the same solvents, probably as a result of the rearrangement being limited by hard desolvation. In this work, a comparative study uncovers the proposed nucleation pathway: difficulty in desolvation has a remarkable effect on the result of rearrangement and nucleation outcome.http://scripts.iucr.org/cgi-bin/paper?S205225252000233Xconformational polymorphsnucleation routesα,ω-alkanedicarboxylic acidsself-assemblyconformational rearrangementintermolecular interactionspolymorphismcrystallization and crystal growth
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Peng Shi Shijie Xu Yiming Ma Weiwei Tang Feng Zhang Jingkang Wang Junbo Gong
spellingShingle	Peng Shi Shijie Xu Yiming Ma Weiwei Tang Feng Zhang Jingkang Wang Junbo Gong Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids IUCrJ conformational polymorphs nucleation routes α,ω-alkanedicarboxylic acids self-assembly conformational rearrangement intermolecular interactions polymorphism crystallization and crystal growth
author_facet	Peng Shi Shijie Xu Yiming Ma Weiwei Tang Feng Zhang Jingkang Wang Junbo Gong
author_sort	Peng Shi
title	Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids
title_short	Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids
title_full	Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids
title_fullStr	Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids
title_full_unstemmed	Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids
title_sort	probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids
publisher	International Union of Crystallography
series	IUCrJ
issn	2052-2525
publishDate	2020-05-01
description	Herein the nucleation pathway of conformational polymorphs was revealed by studying the relationships and distinctions among a series of α,ω-alkanedicarboxylic acids [HOOC–(CH2)n−2–COOH, named DAn, where n = 5, 7, 9, 11, 13, 15] in the solid state and in solution. Their polymorphic outcomes, with the exception of DA5, show solvent dependence: form I with conformation I crystallizes from solvents with hydrogen-bond donating (HBD) ability, whereas form II with conformation II crystallizes preferentially from solvents with no HBD ability. In contrast, form II of DA5 does not crystallize in any of the solvents used. Quantum mechanical computation showed that there is no direct conformational link between the solvents and the resultant polymorphic outcomes. Surprisingly, solute aggregates were found in no-HBD solvents by Fourier transform infrared spectroscopy, and only monomers could be detected in HBD solvents, suggesting stronger solvation. Furthermore, it was found that all six compounds including DA5 followed the same pattern in solution. Moreover, crystal-packing efficiency calculations and stability tests stated that dimorphs of DA5 bear a greater stability difference than others. These suggest that the rearrangement from conformation II to I could not be limited by hard desolvation in HBD solvents, where form I was also obtained. In other systems, metastable II was produced in the same solvents, probably as a result of the rearrangement being limited by hard desolvation. In this work, a comparative study uncovers the proposed nucleation pathway: difficulty in desolvation has a remarkable effect on the result of rearrangement and nucleation outcome.
topic	conformational polymorphs nucleation routes α,ω-alkanedicarboxylic acids self-assembly conformational rearrangement intermolecular interactions polymorphism crystallization and crystal growth
url	http://scripts.iucr.org/cgi-bin/paper?S205225252000233X
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Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

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