Understanding the p-toluenesulfonamide/triphenylphosphine oxide crystal chemistry: A new 1:1 cocrystal and ternary phase diagram

Denise M. Croker; Michael E. Foreman; Bridget N. Hogan; Nuala M. Maguire; Curtis J. Elcoate; Benjamin K. Hodnett; Anita R. Maguire; Ake C. Rasmuson; Simon E. Lawrence

doi:10.1021/cg201300e

Understanding the p-toluenesulfonamide/triphenylphosphine oxide crystal chemistry: A new 1:1 cocrystal and ternary phase diagram

Denise M. Croker, Michael E. Foreman, Bridget N. Hogan, Nuala M. Maguire, Curtis J. Elcoate, Benjamin K. Hodnett, Anita R. Maguire, Ake C. Rasmuson, Simon E. Lawrence

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Abstract

A novel 1:1 cocrystal between p-toluenesulfonamide and triphenylphosphine oxide has been prepared and structurally characterized. This 1:1 cocrystal was observed to form during solid state grinding experiments, with subsequent formation of a known 3:2 cocrystal in the presence of excess sulfonamide. Both cocrystals are stable in the solid state. The ternary phase diagram for the two coformers was constructed in two different solvents: Acetonitrile and dichloromethane. Examination of these diagrams clarified solution crystallization of both the newly discovered 1:1 cocrystal and the previously reported 3:2 cocrystal, and identified regions of stability for each cocrystal in each solvent. The choice of solvent was found to have a significant effect on the position of the solid state regions within a cocrystal system.

Original language	English
Pages (from-to)	869-875
Number of pages	7
Journal	Crystal Growth and Design
Volume	12
Issue number	2
DOIs	https://doi.org/10.1021/cg201300e
Publication status	Published - 1 Feb 2012

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title = "Understanding the p-toluenesulfonamide/triphenylphosphine oxide crystal chemistry: A new 1:1 cocrystal and ternary phase diagram",

abstract = "A novel 1:1 cocrystal between p-toluenesulfonamide and triphenylphosphine oxide has been prepared and structurally characterized. This 1:1 cocrystal was observed to form during solid state grinding experiments, with subsequent formation of a known 3:2 cocrystal in the presence of excess sulfonamide. Both cocrystals are stable in the solid state. The ternary phase diagram for the two coformers was constructed in two different solvents: Acetonitrile and dichloromethane. Examination of these diagrams clarified solution crystallization of both the newly discovered 1:1 cocrystal and the previously reported 3:2 cocrystal, and identified regions of stability for each cocrystal in each solvent. The choice of solvent was found to have a significant effect on the position of the solid state regions within a cocrystal system.",

author = "Croker, \{Denise M.\} and Foreman, \{Michael E.\} and Hogan, \{Bridget N.\} and Maguire, \{Nuala M.\} and Elcoate, \{Curtis J.\} and Hodnett, \{Benjamin K.\} and Maguire, \{Anita R.\} and Rasmuson, \{Ake C.\} and Lawrence, \{Simon E.\}",

year = "2012",

month = feb,

day = "1",

doi = "10.1021/cg201300e",

language = "English",

volume = "12",

pages = "869--875",

journal = "Crystal Growth and Design",

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T1 - Understanding the p-toluenesulfonamide/triphenylphosphine oxide crystal chemistry

T2 - A new 1:1 cocrystal and ternary phase diagram

AU - Croker, Denise M.

AU - Foreman, Michael E.

AU - Hogan, Bridget N.

AU - Maguire, Nuala M.

AU - Elcoate, Curtis J.

AU - Hodnett, Benjamin K.

AU - Maguire, Anita R.

AU - Rasmuson, Ake C.

AU - Lawrence, Simon E.

PY - 2012/2/1

Y1 - 2012/2/1

N2 - A novel 1:1 cocrystal between p-toluenesulfonamide and triphenylphosphine oxide has been prepared and structurally characterized. This 1:1 cocrystal was observed to form during solid state grinding experiments, with subsequent formation of a known 3:2 cocrystal in the presence of excess sulfonamide. Both cocrystals are stable in the solid state. The ternary phase diagram for the two coformers was constructed in two different solvents: Acetonitrile and dichloromethane. Examination of these diagrams clarified solution crystallization of both the newly discovered 1:1 cocrystal and the previously reported 3:2 cocrystal, and identified regions of stability for each cocrystal in each solvent. The choice of solvent was found to have a significant effect on the position of the solid state regions within a cocrystal system.

AB - A novel 1:1 cocrystal between p-toluenesulfonamide and triphenylphosphine oxide has been prepared and structurally characterized. This 1:1 cocrystal was observed to form during solid state grinding experiments, with subsequent formation of a known 3:2 cocrystal in the presence of excess sulfonamide. Both cocrystals are stable in the solid state. The ternary phase diagram for the two coformers was constructed in two different solvents: Acetonitrile and dichloromethane. Examination of these diagrams clarified solution crystallization of both the newly discovered 1:1 cocrystal and the previously reported 3:2 cocrystal, and identified regions of stability for each cocrystal in each solvent. The choice of solvent was found to have a significant effect on the position of the solid state regions within a cocrystal system.

UR - https://www.scopus.com/pages/publications/84858033430

U2 - 10.1021/cg201300e

DO - 10.1021/cg201300e

M3 - Article

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SN - 1528-7483

VL - 12

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JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 2

ER -

Understanding the p-toluenesulfonamide/triphenylphosphine oxide crystal chemistry: A new 1:1 cocrystal and ternary phase diagram

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