Single-crystal X-ray diffraction studies of derivatives of phenolphthalein (3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one)

Brian A. Chalmers; David B. Cordes; Aidan P. McKay; Iain L. J. Patterson; Russell J. Pearson; Joscelyn H. Sequeira-Shuker; Iain A. Smellie; Nadiia Vladymyrova

doi:10.3390/cryst15100901

Single-crystal X-ray diffraction studies of derivatives of phenolphthalein (3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one)

Brian A. Chalmers, David B. Cordes^*, Aidan P. McKay, Iain L. J. Patterson, Russell J. Pearson, Joscelyn H. Sequeira-Shuker, Iain A. Smellie^*, Nadiia Vladymyrova

^*Corresponding author for this work

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

Abstract

An investigation of the molecular structure of a series of phenolphthalein derivatives is presented. The X-ray structures of thymolphthalein, 2,5-dimethylphenolphthalein, and 2,6-dimethylphenolphthalein have been determined for the first time. Furthermore, a series of related 3-(4-hydroxy-dialkyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-ones have also been prepared, and X-ray structures obtained. The present study allows for comparison of the structures of substituted phenolphthalein derivatives, with a particular focus on the effect of different alkyl groups on the structures.

Original language	English
Pages (from-to)	1-15
Number of pages	15
Journal	Crystals
Volume	15
Issue number	10
DOIs	https://doi.org/10.3390/cryst15100901
Publication status	Published - 17 Oct 2025

Keywords

Heterocycle synthesis
Isobenzofuran-1(3H)-ones
pH indicators

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10.3390/cryst15100901Licence: CC BY

Chalmers-et-al-2025-Single-crystal-X-ray-Crystals-15-00901-CCBY
Copyright: © 2025 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Final published version, 1.98 MBLicence: CC BY

Cite this

@article{15a80c0976094adc96a8802d247250fa,

title = "Single-crystal X-ray diffraction studies of derivatives of phenolphthalein (3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one)",

abstract = "An investigation of the molecular structure of a series of phenolphthalein derivatives is presented. The X-ray structures of thymolphthalein, 2,5-dimethylphenolphthalein, and 2,6-dimethylphenolphthalein have been determined for the first time. Furthermore, a series of related 3-(4-hydroxy-dialkyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-ones have also been prepared, and X-ray structures obtained. The present study allows for comparison of the structures of substituted phenolphthalein derivatives, with a particular focus on the effect of different alkyl groups on the structures.",

keywords = "Heterocycle synthesis, Isobenzofuran-1(3H)-ones, pH indicators",

author = "Chalmers, \{Brian A.\} and Cordes, \{David B.\} and McKay, \{Aidan P.\} and Patterson, \{Iain L. J.\} and Pearson, \{Russell J.\} and Sequeira-Shuker, \{Joscelyn H.\} and Smellie, \{Iain A.\} and Nadiia Vladymyrova",

year = "2025",

month = oct,

day = "17",

doi = "10.3390/cryst15100901",

language = "English",

volume = "15",

pages = "1--15",

journal = "Crystals",

issn = "2073-4352",

publisher = "MDPI AG",

number = "10",

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TY - JOUR

T1 - Single-crystal X-ray diffraction studies of derivatives of phenolphthalein (3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one)

AU - Chalmers, Brian A.

AU - Cordes, David B.

AU - McKay, Aidan P.

AU - Patterson, Iain L. J.

AU - Pearson, Russell J.

AU - Sequeira-Shuker, Joscelyn H.

AU - Smellie, Iain A.

AU - Vladymyrova, Nadiia

PY - 2025/10/17

Y1 - 2025/10/17

N2 - An investigation of the molecular structure of a series of phenolphthalein derivatives is presented. The X-ray structures of thymolphthalein, 2,5-dimethylphenolphthalein, and 2,6-dimethylphenolphthalein have been determined for the first time. Furthermore, a series of related 3-(4-hydroxy-dialkyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-ones have also been prepared, and X-ray structures obtained. The present study allows for comparison of the structures of substituted phenolphthalein derivatives, with a particular focus on the effect of different alkyl groups on the structures.

AB - An investigation of the molecular structure of a series of phenolphthalein derivatives is presented. The X-ray structures of thymolphthalein, 2,5-dimethylphenolphthalein, and 2,6-dimethylphenolphthalein have been determined for the first time. Furthermore, a series of related 3-(4-hydroxy-dialkyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-ones have also been prepared, and X-ray structures obtained. The present study allows for comparison of the structures of substituted phenolphthalein derivatives, with a particular focus on the effect of different alkyl groups on the structures.

KW - Heterocycle synthesis

KW - Isobenzofuran-1(3H)-ones

KW - pH indicators

UR - https://www.scopus.com/pages/publications/105019965724

U2 - 10.3390/cryst15100901

DO - 10.3390/cryst15100901

M3 - Article

SN - 2073-4352

VL - 15

SP - 1

EP - 15

JO - Crystals

JF - Crystals

IS - 10

ER -

Single-crystal X-ray diffraction studies of derivatives of phenolphthalein (3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one)

Abstract

Keywords

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CCDC 2492436-2492443: Experimental Crystal Structure Determination

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Single-crystal X-ray diffraction studies of derivatives of phenolphthalein (3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one)

Abstract

Keywords

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Datasets

CCDC 2492436-2492443: Experimental Crystal Structure Determination

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