Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)

The solvent power of the hydrochlorofluoroolefin HCFO-1233 yd.(Z) is investigated using electron-withdrawing and electron-donating substituents on the “parent” (Z)-1-X-2,3,3-trifluoropropene, where X = NH2, OH, CH3O, CH3, F, H, Cl, COOH, CF3, CN, and NO2. The magnitude of the partial atomic charge o...

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Main Authors: A. Fan, H. Zhou, D. Maksuta, R.J. Waltman
Format: Article
Language:English
Published: Elsevier 2025-07-01
Series:Results in Chemistry
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Online Access:http://www.sciencedirect.com/science/article/pii/S2211715625003509
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author A. Fan
H. Zhou
D. Maksuta
R.J. Waltman
author_facet A. Fan
H. Zhou
D. Maksuta
R.J. Waltman
author_sort A. Fan
collection DOAJ
description The solvent power of the hydrochlorofluoroolefin HCFO-1233 yd.(Z) is investigated using electron-withdrawing and electron-donating substituents on the “parent” (Z)-1-X-2,3,3-trifluoropropene, where X = NH2, OH, CH3O, CH3, F, H, Cl, COOH, CF3, CN, and NO2. The magnitude of the partial atomic charge on the 1‑hydrogen atom correlates to the Hammett σ+ substituent constant. The intermolecular interaction between CH3OH and the 1‑hydrogen atom is strengthened by electron-withdrawing 1-substituents producing smaller hydrogen bond distances and larger interaction energies. This work develops a Hammett-based structure-property correlation model to quantify electronic “push–pull” effects in HFO and HCFO solvent systems, guiding HCFO solvent design optimization to enhance its compatibility with PFPE lubricant polarity for hard disk drive application.
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series Results in Chemistry
spelling doaj-art-873f7351fc7c487788b2ea9e128e3c2b2025-08-20T03:43:54ZengElsevierResults in Chemistry2211-71562025-07-011610236710.1016/j.rechem.2025.102367Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)A. Fan0H. Zhou1D. Maksuta2R.J. Waltman3Corresponding author.; Western Digital Corporation, 5601 Great Oaks Parkway, San Jose, CA 95119-1003, USAWestern Digital Corporation, 5601 Great Oaks Parkway, San Jose, CA 95119-1003, USAWestern Digital Corporation, 5601 Great Oaks Parkway, San Jose, CA 95119-1003, USAWestern Digital Corporation, 5601 Great Oaks Parkway, San Jose, CA 95119-1003, USAThe solvent power of the hydrochlorofluoroolefin HCFO-1233 yd.(Z) is investigated using electron-withdrawing and electron-donating substituents on the “parent” (Z)-1-X-2,3,3-trifluoropropene, where X = NH2, OH, CH3O, CH3, F, H, Cl, COOH, CF3, CN, and NO2. The magnitude of the partial atomic charge on the 1‑hydrogen atom correlates to the Hammett σ+ substituent constant. The intermolecular interaction between CH3OH and the 1‑hydrogen atom is strengthened by electron-withdrawing 1-substituents producing smaller hydrogen bond distances and larger interaction energies. This work develops a Hammett-based structure-property correlation model to quantify electronic “push–pull” effects in HFO and HCFO solvent systems, guiding HCFO solvent design optimization to enhance its compatibility with PFPE lubricant polarity for hard disk drive application.http://www.sciencedirect.com/science/article/pii/S2211715625003509HaloolefinsGreen solventsGreen refrigerantsSubstituent effect
spellingShingle A. Fan
H. Zhou
D. Maksuta
R.J. Waltman
Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)
Results in Chemistry
Haloolefins
Green solvents
Green refrigerants
Substituent effect
title Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)
title_full Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)
title_fullStr Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)
title_full_unstemmed Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)
title_short Substituent effects on the solvent power of the haloolefin HCFO-1233 yd.(Z)
title_sort substituent effects on the solvent power of the haloolefin hcfo 1233 yd z
topic Haloolefins
Green solvents
Green refrigerants
Substituent effect
url http://www.sciencedirect.com/science/article/pii/S2211715625003509
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