Hydrogen bonding donation of N-methylformamide with dimethylsulfoxide and water

Borges, Alexandre Luiz Souto; Cordeiro, João Manuel Marques

doi:10.1016/j.cplett.2013.02.017

Cited by 16 publications

(8 citation statements)

References 44 publications

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“…Accordingly, the three molecular pairs reported are very similar [25]. Furthermore, the range of energy distribution (−3 -0 kcal•mol −1 ) is less negative than that observed for NMF or DMSO, for example [37] [38], indicating weak intermolecular interaction in THF, agreeing with the absence of structure suggested based in the g(r) plots. The mono-modal curve observed in Figure 2 is straight in line with the single peak structure of molecular centers distribution function for THF reported [25].…”

Section: Resultssupporting

confidence: 77%

“…Differently of other liquids like acetone and N-methylformamide (NMF) [37] or dimethylsulfoxide (DMSO) and water [38], which present an structured pair energy distribution, consequence of existence of pairs with different stability in the liquids, for THF the pair energy distribution curve show no structure. There is a unique band of energy, indicating that the energy relative to the different pairs corresponding to the OCM is encompassed for that band.…”

Section: Resultsmentioning

confidence: 99%

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Detailing the Structure of Liquid THF Based on an EPSR Study

Borges¹,

Cordeiro

2015

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The structure of pure liquid tetrahydrofuran (THF) has been investigated via Monte Carlo simulations in the wake of a previous Empirical Potential Structure Refinement (EPSR) study on that liquid (Bowron, D.T.; Finney, J.L.; Soper, A.K. (2006) J. Am. Chem. Soc., 128, 5119). The molecules are all-atoms rigid structures and the intermolecular potential used is described for the classical 6-12 Lennard-Jones plus Coulomb in the NPT ensemble at 1 atm and 25˚C. THF is a poorly structured liquid. Typical preferred orientation of molecules has been explored and calculations shown different types of molecular pairs exist concurrently in the liquid. The geometry of those pairs was deeply investigated and its influence in the liquid structure discussed. The lack of molecular organization in the liquid is closely related to the existence of that diversity of molecular pairs. Its geometry changes from antiparallel up to T-like depending on the distance between the molecules in the pairs.

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Detailing the Structure of Liquid THF Based on an EPSR Study

Borges¹,

Cordeiro

2015

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“…However, in the primary amine-ligated NPLs, amines bind to both 3-coordinate surface Cd and Se atoms, the latter in a hydrogen-bonding-like interaction, which is stabilized by a hydrogen-bonding network involving adjacent ligands. , We suggest that NMF ligands bind to surface Cd atoms near ideal stoichiometry, with some residual n -octylamine ligands bound to surface Se atoms, forming hydrogen-bonding networks. We note that NMF is capable of hydrogen bonding …”

Section: Resultsmentioning

confidence: 87%

Halometallates Bind as Z-Type Ligands on Wurtzite CdSe Nanoplatelets

Buhro

2022

Chem. Mater.

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Two-phase ligand exchange of amine-ligated, wurtzite, [CdSe(n-octylamine)0.43(oleylamine)0.07] nanoplatelets with ammonium salts (NH4Cl or [NH4]2[ZnCl4]) or the Lewis acids (ZnCl2 or CdCl2) in N-methylformamide/hexane afford NMF-ligated [CdSe(NMF)0.18(n-octylamine)0.09] nanoplatelets. Subsequent ligand exchanges with the intermediate NMF-ligated nanoplatelets give halometallate-ligated CdSe nanoplatelets having CdX3 – or ZnX4 2– ligands (X = Cl, Br, and I). Two-phase ligand exchange of [CdSe(n-octylamine)0.43(oleylamine)0.07] nanoplatelets with ammonium salts [NH4][CdX3] in N,N-dimethylformamide afford halometallate ligation directly. Analysis of the absorption spectra and X-ray diffraction data of the halometallate-ligated nanoplatelets establish that the halometallates bind as intact, Z-type ligands.

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“…40 A natural starting point for such kind of investigations would be simple amides like N-methylformamide and N-methylacetamide which are models for peptide group linkages, 41,42 Studies of mixtures containing N-methylformamide or N-methylacetamide with neat DMSO have been documented in literature. [42][43][44][45][46][47][48] Borges and Cordeiro 45 have compared the behaviour of 992 Apramita Chand and Snehasis Chowdhuri N-methylformamide in DMSO and water and have found the NMF-DMSO solvation shells to be better structured than in the aqueous one. The study suggested that DMSO may dislodge water molecules bonded to amide structures, promoting dehydration.…”

Section: Introductionmentioning

confidence: 99%

“…It is also observed that NMF-DMSO interactions are stronger than both NMF-NMF 43,44 and NMF-water hydrogen bonds. 45 Infrared studies of Shaw and Li 46 show that DMSO effectively disrupts the inter-amide bonds of Nmethylacetamide by acting as hydrogen bond acceptor to the NH group of NMA. Molecular associations between NMA-DMSO in its binary mixture in benzene solution have been predicted using dielectric relaxation measurements.…”

Section: Introductionmentioning

confidence: 99%

Effects of dimethyl sulfoxide on the hydrogen bonding structure and dynamics of aqueous N-methylacetamide solution

Chand

Chowdhuri

2016

J Chem Sci

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Effects of dimethyl-sulfoxide (DMSO) on the hydrogen bonding structure and dynamics in aqueous N-methylacetamide (NMA) solution are investigated by classical molecular dynamics simulations. The modifications of structure and interaction between water and NMA in presence of DMSO molecules are calculated by various site-site radial distribution functions and average interaction energies between these species in the solution. It is observed that the aqueous peptide hydrogen bond interaction is relatively stronger with increasing concentration of DMSO, whereas methyl-methyl interaction between NMA and DMSO decreases significantly. The DMSO molecule prefers to interact with amide-hydrogen of NMA even at lower DMSO concentration. The lifetimes and structural-relaxation times of NMA-water, water-water and DMSO-water hydrogen bonds are found to increase with increasing DMSO concentration in the solution. The slower translational and rotational dynamics of NMA is observed in concentrated DMSO solution due to formation of stronger inter-species hydrogen bonds in the solution.

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Hydrogen bonding donation of N-methylformamide with dimethylsulfoxide and water

Cited by 16 publications

References 44 publications

Detailing the Structure of Liquid THF Based on an EPSR Study

Detailing the Structure of Liquid THF Based on an EPSR Study

Halometallates Bind as Z-Type Ligands on Wurtzite CdSe Nanoplatelets

Effects of dimethyl sulfoxide on the hydrogen bonding structure and dynamics of aqueous N-methylacetamide solution

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