Intramolecular hydrogen bonds in the sulfonamide derivatives of oxamide, dithiooxamide, and biuret. FT-IR and DFT study, AIM and NBO analysis

Shainyan, B. А.; Chípanina, N. N.; Aksamentova, T. N.; Oznobikhina, Larisa P.; Rosentsveig, G. N.; Rosentsveig, I. B.

doi:10.1016/j.tet.2010.08.076

Cited by 108 publications

(37 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This shows that with increasing the G(r BCP ) value, the covalent characteristic of the chemical bond decreases and becomes nearer to the closed-shell interactions such as majority of the HBs. Therefore, the ratio of −G(r BCP )/V(r BCP ) can be used to quantify the characteristic of HB in the sense that for −G(r BCP )/V(r BCP ) > 1, the HB has non-covalent nature, and for 0.5 < −G(r BCP )/V(r BCP ) < 1 it is partly covalent [39]. Moreover, as explained by Rozas et al [40] in the framework of the QTAIM, HBs can be categorized as weak, medium or strong bonds.…”

Section: Computational Detailsmentioning

confidence: 99%

Computational investigation on the intramolecular resonance-inhibited hydrogen bonding: a new type of interaction versus the RAHB model

Masumian

Nowroozi

2015

Theor Chem Acc

View full text Add to dashboard Cite

Section: Computational Detailsmentioning

confidence: 99%

Computational investigation on the intramolecular resonance-inhibited hydrogen bonding: a new type of interaction versus the RAHB model

Masumian

Nowroozi

2015

Theor Chem Acc

View full text Add to dashboard Cite

“…The calculated parameters for the intramolecular N-H···F bonds along with the lengths of the corresponding hydrogen bonds in the studied complexes are given in Table 3 and topological contour lines of the charge density are shown in Figure 3. [39][40][41] As can be seen in Table 3, the calculated -Gc/Vc values are greater than 1 only in following three intramolecular interactions and therefore these interactions are completely noncovalent: . 37,38 As can be seen, the ρ(BCP) values in the series of these complexes increase when the N-H···X distances decrease.…”

Section: Aim Analysismentioning

confidence: 95%

What causes the weakest host to act as the strongest one? A theoretical study on the host–guest chemistry of five azacryptands and fluoride anions

Salehzadeh

Gholiee

2015

Dalton Trans.

View full text Add to dashboard Cite

In this work we have attempted to computationally analyze the important parameters affecting the selectivity in host-guest systems in order to show that the solvent effect in some host-guest systems is even more important than the hole-size fitting and/or host-guest interaction energy. For this purpose, the fluoride anion selectivities of the five most studied azacryptands with different affinities, moieties, cavity sizes and degrees of preorganization, in their fully protonated forms, were studied at PBE/TZVP and B3P86/TZVP levels of theory. The factors affecting the selectivity such as hole size fitting, steric effects, electronic properties, preorganization of hosts, as well as solvent effects were investigated. The results showed that among the five studied azacryptands, one of them, which ranks fifth for selectivity according to its weak interaction energy with fluoride anions, ranks fourth due to its good preorganization. However, a surprising improvement occurs when its selectivity for fluoride anions ranks first due to the existence of less solvent hindrance. The results of the calculations were further confirmed by a good correlation between the calculated and experimental formation constants.

show abstract

“…Atoms in molecules (AIM)-Bader theory [11] has been extensively applied to demonstrate the presence of intermolecular [12][13][14][15] and intramolecular [17][18][19][20][21][22] hydrogen bonds. According to this theory, upon formation of a chemical bond by two adjacent atoms a bond critical point (BCP) appears between them.…”

Section: Aim Analysismentioning

confidence: 99%

“…Shianyan et al [18] have introduced this parameter for prediction of hydrogen bonds nature. For GVR [ 1 the hydrogen bond has noncovalent nature and for 0.5 \ GVR \ 1 it is relatively covalent.…”

Section: Aim Analysismentioning

confidence: 99%

A computational evidence of the intermolecular/intramolecular hydrogen bonding in salicylsalicylic acid: chemical shielding tensors and AIM analysis

Zahedi-Tabrizi

Ektefa

2015

Monatsh Chem

View full text Add to dashboard Cite

A computational study has been performed at the B3LYP/6-31??G** level to evidence hydrogen bonding interactions in the real crystalline structures of salicylsalicylic acid (salsalate) via chemical shielding tensors at the 17 O nuclei. Real crystalline structure of salsalate reveals two conformers (major and minor). One molecule (monomer), two molecules (dimer), and four molecules (cluster) of conformers of salsalate are modeled by accessible crystal coordinates. The chemical shielding tensors are calculated for three models of both configurations indicating the effect of hydrogen bonding interactions on the NMR parameters. The evaluated NMR parameters of 17 O nuclei of COOH group are significantly alternated from monomer to the target molecule in the dimer due to the contribution in the intermolecular (HO)-C=OÁÁÁH-O-(CO) hydrogen bonds, whereas alternation is insignificant from dimer to the target molecule in the cluster because the number and type of hydrogen bonds do not change. On the other hand, the change in evaluated NMR parameters of 17 O nuclei of (C=)O and O(-H) from the monomer to the target molecule in the dimer and cluster is almost negligible due to the contribution in the intramolecular C=OÁÁÁH-O hydrogen bonds in two conformers. Atoms in molecules (AIM) analysis confirms the presence of hydrogen bondings and vindicates the calculated chemical shielding trends. Graphical abstract

show abstract

Intramolecular hydrogen bonds in the sulfonamide derivatives of oxamide, dithiooxamide, and biuret. FT-IR and DFT study, AIM and NBO analysis

Cited by 108 publications

References 30 publications

Computational investigation on the intramolecular resonance-inhibited hydrogen bonding: a new type of interaction versus the RAHB model

Computational investigation on the intramolecular resonance-inhibited hydrogen bonding: a new type of interaction versus the RAHB model

What causes the weakest host to act as the strongest one? A theoretical study on the host–guest chemistry of five azacryptands and fluoride anions

A computational evidence of the intermolecular/intramolecular hydrogen bonding in salicylsalicylic acid: chemical shielding tensors and AIM analysis

Contact Info

Product

Resources

About