A Rapid Ultrasound Synthesis of Xanthenediones Catalyzed by Boric acid in Ethanol-Water Medium: Single Crystal, DFT and Hirshfeld Surface Analysis of Two Representative Compounds.
Saved in:
| Title: | A Rapid Ultrasound Synthesis of Xanthenediones Catalyzed by Boric acid in Ethanol-Water Medium: Single Crystal, DFT and Hirshfeld Surface Analysis of Two Representative Compounds. |
|---|---|
| Authors: | Shashi, R1 (AUTHOR), Begum, Noor Shahina1 (AUTHOR) noorsb05@gmail.com, Panday, Anoop Kumar2 (AUTHOR) |
| Source: | Journal of Molecular Structure. Mar2021, Vol. 1228, pN.PAG-N.PAG. 1p. |
| Subjects: | Boric acid, Surface analysis, Single crystals, Frontier orbitals, Molecular structure |
| Abstract: | • Ultrasound promoted one pot synthesis of Xanthenediones. • The reactions were carried out by the using boric acid as the catalyst in green solvent medium such as ethanol- water in an efficient manner. • Excellent yields were achieved in short reaction duration. • Two of the products obtained were confirmed by Single crystal X-ray analysis. • DFT calculations have been employed for optimization of these molecules at B3LYP hybrid functional in conjugation with 6-31G (d,p) level of basis sets. • Frontier molecular orbital analysis has been carried out to gain insights into role of different groups towards the HOMO and LUMO of the molecule. • The Mulliken atomic charges and MEP were analyzed for the nucleophilic and electrophilic regions of the molecular surface. A highly versatile and efficient ultrasound promoted synthesis of xanthenedione derivatives is achieved through condensation of dimedone with various aromatic aldehydes using boric acid as catalyst in ethanol-water medium. The advantages of this method being, mild reaction conditions, short reaction time, easy work-up, purification of products by non-chromatographic methods and additionally this method provides excellent yields. Two of the Xanthendiones derivatives 3a and 3b gave good crystals on recrystallization and their molecular structures were confirmed by crystallographic studies. The molecules in the crystal lattice are held together by weak intermolecular C-H•••O and C-H•••N interactions. Further insights into these interactions using Hirshfeld surface analysis and DFT/B3LYP studies show that in compound 3a H•••H (54.7%), O•••H (18.3%) and in 3b H•••H (53.7%), O•••H (17.6%) are the major contributors to the intermolecular interactions which stabilize the crystal structures. In order to determine molecular electrical transport properties, we studied the energy difference between Highest Occupied, HOMO, and Lowest Unoccupied, LUMO orbitals and the HOMO and LUMO energy gap for compounds 3a and 3b was found to be 3.9261 eV and 4.6436 eV respectively. The 2D fingerprint plot provided percentage contribution of each individual atom-to-atom interactions. The Mulliken atomic charges and molecular electrostatic potential on molecular van der Waals surface were calculated to know the electrophilic and nucleophilic regions of the molecular surface. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Molecular Structure is the property of Elsevier B.V. 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.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
|---|---|
| Header | DbId: egs DbLabel: Engineering Source An: 148074391 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
| IllustrationInfo | |
| Items | – Name: Title Label: Title Group: Ti Data: A Rapid Ultrasound Synthesis of Xanthenediones Catalyzed by Boric acid in Ethanol-Water Medium: Single Crystal, DFT and Hirshfeld Surface Analysis of Two Representative Compounds. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Shashi%2C+R%22">Shashi, R</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Begum%2C+Noor+Shahina%22">Begum, Noor Shahina</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> noorsb05@gmail.com</i><br /><searchLink fieldCode="AR" term="%22Panday%2C+Anoop+Kumar%22">Panday, Anoop Kumar</searchLink><relatesTo>2</relatesTo> (AUTHOR) – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Mar2021, Vol. 1228, pN.PAG-N.PAG. 1p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Boric+acid%22">Boric acid</searchLink><br /><searchLink fieldCode="DE" term="%22Surface+analysis%22">Surface analysis</searchLink><br /><searchLink fieldCode="DE" term="%22Single+crystals%22">Single crystals</searchLink><br /><searchLink fieldCode="DE" term="%22Frontier+orbitals%22">Frontier orbitals</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+structure%22">Molecular structure</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: • Ultrasound promoted one pot synthesis of Xanthenediones. • The reactions were carried out by the using boric acid as the catalyst in green solvent medium such as ethanol- water in an efficient manner. • Excellent yields were achieved in short reaction duration. • Two of the products obtained were confirmed by Single crystal X-ray analysis. • DFT calculations have been employed for optimization of these molecules at B3LYP hybrid functional in conjugation with 6-31G (d,p) level of basis sets. • Frontier molecular orbital analysis has been carried out to gain insights into role of different groups towards the HOMO and LUMO of the molecule. • The Mulliken atomic charges and MEP were analyzed for the nucleophilic and electrophilic regions of the molecular surface. A highly versatile and efficient ultrasound promoted synthesis of xanthenedione derivatives is achieved through condensation of dimedone with various aromatic aldehydes using boric acid as catalyst in ethanol-water medium. The advantages of this method being, mild reaction conditions, short reaction time, easy work-up, purification of products by non-chromatographic methods and additionally this method provides excellent yields. Two of the Xanthendiones derivatives 3a and 3b gave good crystals on recrystallization and their molecular structures were confirmed by crystallographic studies. The molecules in the crystal lattice are held together by weak intermolecular C-H•••O and C-H•••N interactions. Further insights into these interactions using Hirshfeld surface analysis and DFT/B3LYP studies show that in compound 3a H•••H (54.7%), O•••H (18.3%) and in 3b H•••H (53.7%), O•••H (17.6%) are the major contributors to the intermolecular interactions which stabilize the crystal structures. In order to determine molecular electrical transport properties, we studied the energy difference between Highest Occupied, HOMO, and Lowest Unoccupied, LUMO orbitals and the HOMO and LUMO energy gap for compounds 3a and 3b was found to be 3.9261 eV and 4.6436 eV respectively. The 2D fingerprint plot provided percentage contribution of each individual atom-to-atom interactions. The Mulliken atomic charges and molecular electrostatic potential on molecular van der Waals surface were calculated to know the electrophilic and nucleophilic regions of the molecular surface. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. 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.) |
| PLink | https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=148074391 |
| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1016/j.molstruc.2020.129794 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 1 StartPage: N.PAG Subjects: – SubjectFull: Boric acid Type: general – SubjectFull: Surface analysis Type: general – SubjectFull: Single crystals Type: general – SubjectFull: Frontier orbitals Type: general – SubjectFull: Molecular structure Type: general Titles: – TitleFull: A Rapid Ultrasound Synthesis of Xanthenediones Catalyzed by Boric acid in Ethanol-Water Medium: Single Crystal, DFT and Hirshfeld Surface Analysis of Two Representative Compounds. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Shashi, R – PersonEntity: Name: NameFull: Begum, Noor Shahina – PersonEntity: Name: NameFull: Panday, Anoop Kumar IsPartOfRelationships: – BibEntity: Dates: – D: 15 M: 03 Text: Mar2021 Type: published Y: 2021 Identifiers: – Type: issn-print Value: 00222860 Numbering: – Type: volume Value: 1228 Titles: – TitleFull: Journal of Molecular Structure Type: main |
| ResultId | 1 |
