Cover Image

Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis

The simultaneous presence of sulfate and hydrogen sulfate in the crystal structure of an organic molten salt was demonstrated by single-crystal X-ray diffraction. The plenty of intra-hydrogen bonding between the dication of the protonated 1,3-di(4-piperidinyl)propane (TMDP), anions of sulfate and hy...

Full description

Saved in:
Bibliographic Details
Main Authors: Zaharani, Lia, Rafie, Mohd Johan, Khaligh, Nader Ghaffari
Format: Article
Published: Elsevier 2024
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://eprints.um.edu.my/44730/
https://doi.org/10.1016/j.molstruc.2024.137621
Tags: Add Tag
No Tags, Be the first to tag this record!
id my.um.eprints.44730
record_format eprints
spelling my.um.eprints.447302024-11-15T03:33:06Z http://eprints.um.edu.my/44730/ Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis Zaharani, Lia Rafie, Mohd Johan Khaligh, Nader Ghaffari Q Science (General) QD Chemistry The simultaneous presence of sulfate and hydrogen sulfate in the crystal structure of an organic molten salt was demonstrated by single-crystal X-ray diffraction. The plenty of intra-hydrogen bonding between the dication of the protonated 1,3-di(4-piperidinyl)propane (TMDP), anions of sulfate and hydrogen sulfate, and crystalline water, as well as the existence of Brönsted acid of HSO4− gives a strong ionic network. Spectroscopic and single-crystal studies reveal that the origin of superior binding for organic molten salt is correlated with the formation of strong hydrogen bonds between organic dications, sulfate and hydrogen sulfate anions, and crystalline waters. Though FTIR spectroscopy is a useful tool to prove the presence of sulfate or hydrogen sulfate, the existence of simultaneous HSO4− and SO42− cannot be differentiated from the presence of HSO4− by the FTIR spectrum. Two protonated piperidinyl rings were in the chair conformation. The tetrahedral geometry was observed around sulfur atoms in sulfate and hydrogen sulfate ions. This salt is another sample of unique organic molten salts in the sense that both sulfate and hydrogen sulfate anions are simultaneously linked through hydrogen bonds with the protonated piperidinyl rings of TMDP in one unit cell; nevertheless, there is no direct hydrogen bond between hydrogen sulfate and sulfate anions. Its unit cell contains two protonated TMDP, one sulfate, two hydrogen sulfate, and three crystalline waters. The crystal structure is stabilized by classical NsbndH⋯O and OsbndH⋯O hydrogen bonds, generating a strong three-dimensional network. In addition, the catalytic activity of the organic salt was demonstrated by preparing various 3,4,5-trisubstituted furan-2-one using a catalytic amount of the organic salt under mild and greener conditions owing to the existence of donor-acceptor hydrogen bonding sites and the presence of Brönsted acid anion. © 2024 Elsevier B.V. Elsevier 2024 Article PeerReviewed Zaharani, Lia and Rafie, Mohd Johan and Khaligh, Nader Ghaffari (2024) Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis. Journal of Molecular Structure, 1304. p. 137621. ISSN 0022-2860, DOI https://doi.org/10.1016/j.molstruc.2024.137621 <https://doi.org/10.1016/j.molstruc.2024.137621>. https://doi.org/10.1016/j.molstruc.2024.137621 10.1016/j.molstruc.2024.137621
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic Q Science (General)
QD Chemistry
spellingShingle Q Science (General)
QD Chemistry
Zaharani, Lia
Rafie, Mohd Johan
Khaligh, Nader Ghaffari
Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis
description The simultaneous presence of sulfate and hydrogen sulfate in the crystal structure of an organic molten salt was demonstrated by single-crystal X-ray diffraction. The plenty of intra-hydrogen bonding between the dication of the protonated 1,3-di(4-piperidinyl)propane (TMDP), anions of sulfate and hydrogen sulfate, and crystalline water, as well as the existence of Brönsted acid of HSO4− gives a strong ionic network. Spectroscopic and single-crystal studies reveal that the origin of superior binding for organic molten salt is correlated with the formation of strong hydrogen bonds between organic dications, sulfate and hydrogen sulfate anions, and crystalline waters. Though FTIR spectroscopy is a useful tool to prove the presence of sulfate or hydrogen sulfate, the existence of simultaneous HSO4− and SO42− cannot be differentiated from the presence of HSO4− by the FTIR spectrum. Two protonated piperidinyl rings were in the chair conformation. The tetrahedral geometry was observed around sulfur atoms in sulfate and hydrogen sulfate ions. This salt is another sample of unique organic molten salts in the sense that both sulfate and hydrogen sulfate anions are simultaneously linked through hydrogen bonds with the protonated piperidinyl rings of TMDP in one unit cell; nevertheless, there is no direct hydrogen bond between hydrogen sulfate and sulfate anions. Its unit cell contains two protonated TMDP, one sulfate, two hydrogen sulfate, and three crystalline waters. The crystal structure is stabilized by classical NsbndH⋯O and OsbndH⋯O hydrogen bonds, generating a strong three-dimensional network. In addition, the catalytic activity of the organic salt was demonstrated by preparing various 3,4,5-trisubstituted furan-2-one using a catalytic amount of the organic salt under mild and greener conditions owing to the existence of donor-acceptor hydrogen bonding sites and the presence of Brönsted acid anion. © 2024 Elsevier B.V.
format Article
author Zaharani, Lia
Rafie, Mohd Johan
Khaligh, Nader Ghaffari
author_facet Zaharani, Lia
Rafie, Mohd Johan
Khaligh, Nader Ghaffari
author_sort Zaharani, Lia
title Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis
title_short Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis
title_full Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis
title_fullStr Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis
title_full_unstemmed Bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: An organic molten salt containing simultaneous acceptor-donor hydrogen bonding and Brönsted acid for homogeneous catalysis
title_sort bis[1,3-di(4-piperidinium)propane] di-hydrogensulfate mono-sulfate trihydrate: an organic molten salt containing simultaneous acceptor-donor hydrogen bonding and brönsted acid for homogeneous catalysis
publisher Elsevier
publishDate 2024
url http://eprints.um.edu.my/44730/
https://doi.org/10.1016/j.molstruc.2024.137621
_version_ 1816130419218710528
score 13.223943

Similar Items