The S–H⋯N versus O–H⋯N hydrogen bonding in the ammonia complexes with CH3OH and CH3SH

Grzechnik, Katarzyna; Rutkowski, K.S.; Mielke, Zofia

doi:10.1016/j.molstruc.2011.10.015

Cited by 28 publications

(12 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…S system where the sulfur atom acts as the H acceptor. − In their book, The Hydrogen Bond , Pimentel and McClellan specifically mentioned the S–H group as a possible H-bond donor with the S–H stretching mode broadening, shifting to lower frequency and becoming much more intense . However, few recent studies have been reported for complexes with the sulfur atom playing the role of H-bond donor in S–H···Y type interactions, − with the efforts of Wategaonkar and co-workers a notable exception.…”

Section: Introductionmentioning

confidence: 99%

Thiols as Hydrogen Bond Acceptors and Donors: Spectroscopy of 2-Phenylethanethiol Complexes

et al. 2018

View full text Add to dashboard Cite

Evidence and understanding of sulfur-centered hydrogen bonding, especially where the donor is a thiol, lags far behind that for conventional OH interactions. To help address this deficiency, conformer specific IR spectra of 2-phenylethanethiol (PET) and associated 1:1 solvent complexes have been measured in SH, OH, and CH stretch regions using resonant-two-photon-ionization (R2PI) and IR-UV ion dip spectroscopic techniques. The aromatic and aliphatic CH stretch regions show signature differences between anti and gauche conformers. Supported by ab initio calculations, a PET-water cluster with an OH···S arrangement and a PET-diethyl ether cluster expressing an SH···O interaction were identified. The SH stretch band of the SH···O complex is red-shifted and undergoes significant intensity enhancement compared to the bare molecule, which is characteristic of hydrogen bonding. These findings offer insight into the nature of the thiol functional group as a potential hydrogen bond donor and acceptor.

show abstract

Section: Introductionmentioning

confidence: 99%

Thiols as Hydrogen Bond Acceptors and Donors: Spectroscopy of 2-Phenylethanethiol Complexes

et al. 2018

View full text Add to dashboard Cite

show abstract

“…There is an assortment of different noncovalent forces, among which the hydrogen bond (HB) has been intensively studied over a long period of time. [1][2][3][4] Earlier ideas about the nature of HBs in which the proton donor and acceptor atoms are F, O, or N has slowly been modernized to a more generalized scheme which includes less electronegative atoms like Cl, S, or C, [5][6][7][8][9] and the idea that the bridging proton interacts with a lone electron pair has been extended to p and s bonds, [10][11][12][13][14] and even to a hydridic H atom within the context of dihydrogen bonds. 12,[15][16][17][18] A different but related class of noncovalent bond is associated with the attraction between a pair of electronegative atoms.…”

Section: Introductionmentioning

confidence: 99%

Complexes containing CO₂and SO₂. Mixed dimers, trimers and tetramers

Azofra

Scheiner

2014

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

Mixed dimers, trimers and tetramers composed of SO2 and CO2 molecules are examined by ab initio calculations to identify all minimum energy structures. While AIM formalism leads to the idea of a pair of C···O bonds in the most stable heterodimer, bound by some 2 kcal mol(-1), NBO analysis describes the bonding in terms of charge transfer from O lone pairs of SO2 to the CO π* antibonding orbitals. The second minimum on the surface, just slightly less stable, is described by AIM as containing a single O···O chalcogen bond. The NBO picture is that of two transfers in opposite directions: one from a SO2 O lone pair to a π* antibond of CO2, supplemented by CO2 Olp → π*(SO). Decomposition of the interaction energies points to electrostatic attraction and dispersion as the dominant attractive components, in roughly equal measure. The various heterotrimers and tetramers generally retain the dimer structure as a starting point. Cyclic oligomers are favored over linear geometries, with a preference for complexes containing larger numbers of SO2 molecules.

show abstract

“…On the other hand, detailed studies of the hydrogen-bonds involving an unconventional hydrogen-bond donor are mostly limited to C–H···Y hydrogen-bonds, where Y is generally a conventional hydrogen-bond acceptor (O, N, etc. ), and this hydrogen-bond has been established as a weak non-covalent interaction. ,− Nevertheless, there are a few spectroscopic studies in the literature involving S as a hydrogen-bond donor with a π-electron cloud as well as N and O acting as hydrogen-bond acceptors. − These reports suggest that S, in general, is a weak hydrogen-bond donor as compared to N and O.…”

mentioning

confidence: 99%

Observation of an Unusually Large IR Red-Shift in an Unconventional S–H···S Hydrogen-Bond

Mishra

Borish

Singh

et al. 2021

J. Phys. Chem. Lett.

View full text Add to dashboard Cite

The S–H···S non-covalent interaction is generally known as an extremely unconventional weak hydrogen-bond in the literature. The present gas-phase spectroscopic investigation shows that the S–H···S hydrogen-bond can be as strong as any conventional hydrogen-bond in terms of the IR red-shift in the stretching frequency of the hydrogen-bond donor group. Herein, the strength of the S–H···S hydrogen-bond has been determined by measuring the red-shift (∼150 cm–1) of the S–H stretching frequency in a model complex of 2-chlorothiophenol and dimethyl sulfide using isolated gas-phase IR spectroscopy coupled with quantum chemistry calculations. The observation of an unusually large IR red-shift in the S–H···S hydrogen-bond is explained in terms of the presence of a significant amount of charge-transfer interactions in addition to the usual electrostatic interactions. The existence of ∼750 S–H···S interactions between the cysteine and methionine residues in 642 protein structures determined from an extensive Protein Data Bank analysis also indicates that this interaction is important for the structures of proteins.

show abstract

The S–H⋯N versus O–H⋯N hydrogen bonding in the ammonia complexes with CH3OH and CH3SH

Cited by 28 publications

References 45 publications

Thiols as Hydrogen Bond Acceptors and Donors: Spectroscopy of 2-Phenylethanethiol Complexes

Thiols as Hydrogen Bond Acceptors and Donors: Spectroscopy of 2-Phenylethanethiol Complexes

Complexes containing CO₂and SO₂. Mixed dimers, trimers and tetramers

Observation of an Unusually Large IR Red-Shift in an Unconventional S–H···S Hydrogen-Bond

Contact Info

Product

Resources

About

The S–H⋯N versus O–H⋯N hydrogen bonding in the ammonia complexes with CH3OH and CH3SH

Cited by 28 publications

References 45 publications

Thiols as Hydrogen Bond Acceptors and Donors: Spectroscopy of 2-Phenylethanethiol Complexes

Thiols as Hydrogen Bond Acceptors and Donors: Spectroscopy of 2-Phenylethanethiol Complexes

Complexes containing CO2and SO2. Mixed dimers, trimers and tetramers

Observation of an Unusually Large IR Red-Shift in an Unconventional S–H···S Hydrogen-Bond

Contact Info

Product

Resources

About

Complexes containing CO₂and SO₂. Mixed dimers, trimers and tetramers