Hierarchical Molecular Structure–Based Method to Estimate the Normal Boiling Point of Aliphatic Oxygen‐Containing Organic Compounds.
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| Title: | Hierarchical Molecular Structure–Based Method to Estimate the Normal Boiling Point of Aliphatic Oxygen‐Containing Organic Compounds. |
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| Authors: | Long, Jincan1 (AUTHOR), Cao, Chao‐Tun1 (AUTHOR) caoztchem@163.com, Cao, Chenzhong1 (AUTHOR) czcao@hnust.edu.cn |
| Source: | Journal of Physical Organic Chemistry. Jul2025, Vol. 38 Issue 7, p1-11. 11p. |
| Subjects: | Boiling-points, Molecular structure, Organic compounds, Carboxylic acids, Ketones, Aliphatic alcohols |
| Abstract: | In this work, a hierarchical molecular structure method (HMSM) was proposed to extract molecular descriptors. In this method, the molecular structure is divided into three hierarchies: the first hierarchy involves the contributions of the number of vertices (vertex number m and the sum of vertex number effect, SVNE); the second hierarchy involves the contributions of the vertex skeleton (odd‐even index, OEI, and intramolecular polarization effect index, IMPEI); and the third hierarchy involves the contributions of the functional group (polarization effect index, PEI, and group influencing factor, GN). Using these six molecular descriptors, the normal boiling points (NBP) of aliphatic oxygen‐containing organic compounds (AOCOCs), including alcohols, ethers, aldehydes, ketones, carboxylic acids, and esters, can be quantitatively correlated well. The results show that the average absolute percentage error (APPE) between the experimental and calculated NBP values for each series of AOCOCs is less than 1%. Based on the obtained QSPR models, the NBPs of some AOCOCs that have not been experimentally measured were predicted, including 14 alcohols, 25 ethers, 106 aldehydes, 72 ketones, 103 carboxylic acids, and 57 esters. Additionally, a QSPR model for all 518 AOCOCs was also derived, yielding an APPE value of only 1.35%, indicating that the HMSM‐based QSPR model performs exceptionally well in the field of QSPR modeling. The specific contributions of functional groups to NBP were discussed and their order is as follows: COOH > OH > COO > C(O) > CHO > O. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Physical Organic Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
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| Header | DbId: egs DbLabel: Engineering Source An: 186049919 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Hierarchical Molecular Structure–Based Method to Estimate the Normal Boiling Point of Aliphatic Oxygen‐Containing Organic Compounds. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Long%2C+Jincan%22">Long, Jincan</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Cao%2C+Chao‐Tun%22">Cao, Chao‐Tun</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> caoztchem@163.com</i><br /><searchLink fieldCode="AR" term="%22Cao%2C+Chenzhong%22">Cao, Chenzhong</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> czcao@hnust.edu.cn</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Physical+Organic+Chemistry%22">Journal of Physical Organic Chemistry</searchLink>. Jul2025, Vol. 38 Issue 7, p1-11. 11p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Boiling-points%22">Boiling-points</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+structure%22">Molecular structure</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+compounds%22">Organic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Carboxylic+acids%22">Carboxylic acids</searchLink><br /><searchLink fieldCode="DE" term="%22Ketones%22">Ketones</searchLink><br /><searchLink fieldCode="DE" term="%22Aliphatic+alcohols%22">Aliphatic alcohols</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: In this work, a hierarchical molecular structure method (HMSM) was proposed to extract molecular descriptors. In this method, the molecular structure is divided into three hierarchies: the first hierarchy involves the contributions of the number of vertices (vertex number m and the sum of vertex number effect, SVNE); the second hierarchy involves the contributions of the vertex skeleton (odd‐even index, OEI, and intramolecular polarization effect index, IMPEI); and the third hierarchy involves the contributions of the functional group (polarization effect index, PEI, and group influencing factor, GN). Using these six molecular descriptors, the normal boiling points (NBP) of aliphatic oxygen‐containing organic compounds (AOCOCs), including alcohols, ethers, aldehydes, ketones, carboxylic acids, and esters, can be quantitatively correlated well. The results show that the average absolute percentage error (APPE) between the experimental and calculated NBP values for each series of AOCOCs is less than 1%. Based on the obtained QSPR models, the NBPs of some AOCOCs that have not been experimentally measured were predicted, including 14 alcohols, 25 ethers, 106 aldehydes, 72 ketones, 103 carboxylic acids, and 57 esters. Additionally, a QSPR model for all 518 AOCOCs was also derived, yielding an APPE value of only 1.35%, indicating that the HMSM‐based QSPR model performs exceptionally well in the field of QSPR modeling. The specific contributions of functional groups to NBP were discussed and their order is as follows: COOH > OH > COO > C(O) > CHO > O. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Physical Organic Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1002/poc.70020 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 11 StartPage: 1 Subjects: – SubjectFull: Boiling-points Type: general – SubjectFull: Molecular structure Type: general – SubjectFull: Organic compounds Type: general – SubjectFull: Carboxylic acids Type: general – SubjectFull: Ketones Type: general – SubjectFull: Aliphatic alcohols Type: general Titles: – TitleFull: Hierarchical Molecular Structure–Based Method to Estimate the Normal Boiling Point of Aliphatic Oxygen‐Containing Organic Compounds. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Long, Jincan – PersonEntity: Name: NameFull: Cao, Chao‐Tun – PersonEntity: Name: NameFull: Cao, Chenzhong IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 07 Text: Jul2025 Type: published Y: 2025 Identifiers: – Type: issn-print Value: 08943230 Numbering: – Type: volume Value: 38 – Type: issue Value: 7 Titles: – TitleFull: Journal of Physical Organic Chemistry Type: main |
| ResultId | 1 |
