Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids:  Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon

Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids:  Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon

A group of caffeine-containing co-crystals of hydroxy-2-naphthoic acids were synthesized and analyzed via single-crystal X-ray diffraction and IR analysis. The imidazole−carboxylic acid synthon was observed in co-crystals involving 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acid. In the case of...

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Veröffentlicht in:Molecular pharmaceutics 2007-05, Vol.4 (3), p.339-346
Hauptverfasser: Bučar, Dejan-Krešimir, Henry, Rodger F., Lou, Xiaochun, Duerst, Richard W., Borchardt, Thomas B., MacGillivray, Leonard R., Zhang, Geoff G. Z.
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Sprache:eng
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Caffeine - chemistry
Carboxylic Acids - chemistry
Crystallization
Crystallography, X-Ray
Dimerization
Hydrogen Bonding
Models, Molecular
Molecular Structure
Naphthols - chemistry
Powder Diffraction
Spectroscopy, Fourier Transform Infrared
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container_end_page 346
container_issue 3
container_start_page 339
container_title Molecular pharmaceutics
container_volume 4
creator Bučar, Dejan-Krešimir
Henry, Rodger F.
Lou, Xiaochun
Duerst, Richard W.
Borchardt, Thomas B.
MacGillivray, Leonard R.
Zhang, Geoff G. Z.
description A group of caffeine-containing co-crystals of hydroxy-2-naphthoic acids were synthesized and analyzed via single-crystal X-ray diffraction and IR analysis. The imidazole−carboxylic acid synthon was observed in co-crystals involving 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acid. In the case of 6-hydroxy-2-naphthoic acid, the co-crystal exhibits a hydrogen-bonded carboxylic acid dimer in the presence of a hydroxyl−caffeine heterosynthon. Keywords: Pharmaceutical co-crystals; co-crystal screening; hydrogen bond; caffeine; naphthoic acid; supramolecular synthon; crystal engineering; 1-hydroxy-2-naphthoic acid; 3-hydroxy-2-naphthoic acid; 6-hydroxy-2-naphthoic acid
doi_str_mv 10.1021/mp070004b
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Z.</creatorcontrib><title>Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids:  Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon</title><title>Molecular pharmaceutics</title><addtitle>Mol. Pharmaceutics</addtitle><description>A group of caffeine-containing co-crystals of hydroxy-2-naphthoic acids were synthesized and analyzed via single-crystal X-ray diffraction and IR analysis. The imidazole−carboxylic acid synthon was observed in co-crystals involving 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acid. In the case of 6-hydroxy-2-naphthoic acid, the co-crystal exhibits a hydrogen-bonded carboxylic acid dimer in the presence of a hydroxyl−caffeine heterosynthon. 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Keywords: Pharmaceutical co-crystals; co-crystal screening; hydrogen bond; caffeine; naphthoic acid; supramolecular synthon; crystal engineering; 1-hydroxy-2-naphthoic acid; 3-hydroxy-2-naphthoic acid; 6-hydroxy-2-naphthoic acid</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17489605</pmid><doi>10.1021/mp070004b</doi><tpages>8</tpages></addata></record>
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source MEDLINE; ACS Publications
subjects Caffeine - chemistry
Carboxylic Acids - chemistry
Crystallization
Crystallography, X-Ray
Dimerization
Hydrogen Bonding
Models, Molecular
Molecular Structure
Naphthols - chemistry
Powder Diffraction
Spectroscopy, Fourier Transform Infrared
title Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids:  Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon
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