One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT

<p dir="ltr">The(3R,4R,6R)-3-(((E)-2-hydroxybenzylidene)amino)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol water-soluble Glucose amine Schiff base (GASB-1) product was made available by condensation of 2-hydroxybenzaldehyde with (3R,6R)-3-amino-6-(hydroxymethyl)-tetra-hydro-2H-p...

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Main Author: Yousef Hijji (17860688) (author)
Other Authors: Rajeesha Rajan (19645942) (author), Hamdi Ben Yahia (9662822) (author), Said Mansour (8697699) (author), Abdelkader Zarrouk (1900912) (author), Ismail Warad (7120355) (author)
Published: 2021
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_version_ 1864513505694056448
author Yousef Hijji (17860688)
author2 Rajeesha Rajan (19645942)
Hamdi Ben Yahia (9662822)
Said Mansour (8697699)
Abdelkader Zarrouk (1900912)
Ismail Warad (7120355)
author2_role author
author
author
author
author
author_facet Yousef Hijji (17860688)
Rajeesha Rajan (19645942)
Hamdi Ben Yahia (9662822)
Said Mansour (8697699)
Abdelkader Zarrouk (1900912)
Ismail Warad (7120355)
author_role author
dc.creator.none.fl_str_mv Yousef Hijji (17860688)
Rajeesha Rajan (19645942)
Hamdi Ben Yahia (9662822)
Said Mansour (8697699)
Abdelkader Zarrouk (1900912)
Ismail Warad (7120355)
dc.date.none.fl_str_mv 2021-01-26T03:00:00Z
dc.identifier.none.fl_str_mv 10.3390/cryst11020117
dc.relation.none.fl_str_mv https://figshare.com/articles/journal_contribution/One-Pot_Microwave-Assisted_Synthesis_of_Water-Soluble_Pyran-2_4_5-triol_Glucose_Amine_Schiff_Base_Derivative_XRD_HSA_Interactions_Crystal_Structure_Spectral_Thermal_and_a_DFT_TD-DFT/26983888
dc.rights.none.fl_str_mv CC BY 4.0
info:eu-repo/semantics/openAccess
dc.subject.none.fl_str_mv Chemical sciences
Inorganic chemistry
Theoretical and computational chemistry
Engineering
Materials engineering
crystal structure
Schiff base
DFT
glucose amine
salicylaldehyde
dc.title.none.fl_str_mv One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
dc.type.none.fl_str_mv Text
Journal contribution
info:eu-repo/semantics/publishedVersion
text
contribution to journal
description <p dir="ltr">The(3R,4R,6R)-3-(((E)-2-hydroxybenzylidene)amino)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol water-soluble Glucose amine Schiff base (GASB-1) product was made available by condensation of 2-hydroxybenzaldehyde with (3R,6R)-3-amino-6-(hydroxymethyl)-tetra-hydro-2H-pyran-2,4,5-triol under mono-mode microwave heating. A one-pot 5-minute microwave-assisted reaction was required to complete the condensation reaction with 90% yield and without having byproducts. The 3D structure of GASB-1 was solved from single crystal X-ray diffraction data and computed by DFT/6-311G(d,p). The Hirshfeld surface analysis (HSA), molecular electronic potential (MEP), Mulliken atomic charge (MAC), and natural population analysis (NPA) were performed. The IR and UV-Vis spectra were matched to their density functional theory (DFT) relatives and the thermal behavior was resolved in an open-room condition via thermogravimetry/Derivative thermogravimetry (TG/DTG) and differential scanning calorimetry (DSC). The highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO), density of state (DOS), and time-dependence TD-DFT computations were correlated to the experimental electron transfer in water and acrylonitrile solvents.</p><h2>Other Information</h2><p dir="ltr">Published in: Crystals<br>License: <a href="https://creativecommons.org/licenses/by/4.0/" target="_blank">https://creativecommons.org/licenses/by/4.0/</a><br>See article on publisher's website: <a href="https://dx.doi.org/10.3390/cryst11020117" target="_blank">https://dx.doi.org/10.3390/cryst11020117</a></p>
eu_rights_str_mv openAccess
id Manara2_320635ede3ea549f716870962f320993
identifier_str_mv 10.3390/cryst11020117
network_acronym_str Manara2
network_name_str Manara2
oai_identifier_str oai:figshare.com:article/26983888
publishDate 2021
repository.mail.fl_str_mv
repository.name.fl_str_mv
repository_id_str
rights_invalid_str_mv CC BY 4.0
spelling One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFTYousef Hijji (17860688)Rajeesha Rajan (19645942)Hamdi Ben Yahia (9662822)Said Mansour (8697699)Abdelkader Zarrouk (1900912)Ismail Warad (7120355)Chemical sciencesInorganic chemistryTheoretical and computational chemistryEngineeringMaterials engineeringcrystal structureSchiff baseDFTglucose aminesalicylaldehyde<p dir="ltr">The(3R,4R,6R)-3-(((E)-2-hydroxybenzylidene)amino)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol water-soluble Glucose amine Schiff base (GASB-1) product was made available by condensation of 2-hydroxybenzaldehyde with (3R,6R)-3-amino-6-(hydroxymethyl)-tetra-hydro-2H-pyran-2,4,5-triol under mono-mode microwave heating. A one-pot 5-minute microwave-assisted reaction was required to complete the condensation reaction with 90% yield and without having byproducts. The 3D structure of GASB-1 was solved from single crystal X-ray diffraction data and computed by DFT/6-311G(d,p). The Hirshfeld surface analysis (HSA), molecular electronic potential (MEP), Mulliken atomic charge (MAC), and natural population analysis (NPA) were performed. The IR and UV-Vis spectra were matched to their density functional theory (DFT) relatives and the thermal behavior was resolved in an open-room condition via thermogravimetry/Derivative thermogravimetry (TG/DTG) and differential scanning calorimetry (DSC). The highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO), density of state (DOS), and time-dependence TD-DFT computations were correlated to the experimental electron transfer in water and acrylonitrile solvents.</p><h2>Other Information</h2><p dir="ltr">Published in: Crystals<br>License: <a href="https://creativecommons.org/licenses/by/4.0/" target="_blank">https://creativecommons.org/licenses/by/4.0/</a><br>See article on publisher's website: <a href="https://dx.doi.org/10.3390/cryst11020117" target="_blank">https://dx.doi.org/10.3390/cryst11020117</a></p>2021-01-26T03:00:00ZTextJournal contributioninfo:eu-repo/semantics/publishedVersiontextcontribution to journal10.3390/cryst11020117https://figshare.com/articles/journal_contribution/One-Pot_Microwave-Assisted_Synthesis_of_Water-Soluble_Pyran-2_4_5-triol_Glucose_Amine_Schiff_Base_Derivative_XRD_HSA_Interactions_Crystal_Structure_Spectral_Thermal_and_a_DFT_TD-DFT/26983888CC BY 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/269838882021-01-26T03:00:00Z
spellingShingle One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
Yousef Hijji (17860688)
Chemical sciences
Inorganic chemistry
Theoretical and computational chemistry
Engineering
Materials engineering
crystal structure
Schiff base
DFT
glucose amine
salicylaldehyde
status_str publishedVersion
title One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
title_full One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
title_fullStr One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
title_full_unstemmed One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
title_short One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
title_sort One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT
topic Chemical sciences
Inorganic chemistry
Theoretical and computational chemistry
Engineering
Materials engineering
crystal structure
Schiff base
DFT
glucose amine
salicylaldehyde