A computational study of the interactions of the caespitate molecule with water

Mammino, Liliana; Kabanda, Mwadham M.

doi:10.1002/qua.21594

Cited by 29 publications

(8 citation statements)

References 48 publications

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“…IHBs have significant roles in stabilising molecular conformations and in influencing biological activities [49][50][51][52][53][54][55][56][57][58][59][60][61]. LD and LR have two conformations (LD t -1a and LD t -1b, and LR t -1a and LR t -1b, respectively) that are stabilised by the presence of IHB, resulting in the formation of H-bond quasi-rings.…”

Section: Tautomeric Stability Conformational Preferences and Aim Anamentioning

confidence: 99%

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

et al. 2014

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Theoretical studies on lucidone, linderone and methyllinderone were performed to investigate factors that contribute to structural stability and to elucidate the antioxidant properties and mechanisms. The study was performed in different media utilising the density functional theory with different functionals and the 6-311 + G(d,p) basis set. The antioxidant activity has been considered through the electron transfer and metal chelation mechanisms. The results show that the stability of the tautomers and conformers is due to the presence of several intramolecular hydrogen bonds. The ionisation potential values suggest that the antiradical activity increases with the increase in the number of OCH 3 groups substituted on the cyclopentene-1,3-dione ring. In vacuo, the spin density of the Fe(II) cation upon ligand coordination decreases to 3.0−3.5, whereas the ligand spin density approaches 1, indicating that it is oxidised to a radical cation. The metal ion affinity (MIA) is influenced by the position and number of OCH 3 substituted on the acylcyclopentene-1,3-dione ring. A very favourable MIA, in vacuo, is obtained when Fe(II) is chelated between the sp 2 O and sp 3 O atoms. An estimation of MIA in an aqueous solution shows a remarkable decrease with respect to the results in vacuo.

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Section: Tautomeric Stability Conformational Preferences and Aim Anamentioning

confidence: 99%

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

et al. 2014

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“…The consideration of explicit water molecule is important in the case that the water molecule can form hydrogen bond(s) with the solute molecule, because this aspect may not be taken into account by available SCRF theory, such as PCM models. 52,53 Trimer structures of T1-T3 and T4-T9 with water molecules being located at different positions of D1 and D2 have been optimized at the PBE1PBE/6-31G* level. The structures and binding energies are given in Fig.…”

Section: Interaction Of H 4 Tppcl 2 Dimer With Watermentioning

confidence: 99%

Theoretical study of intermolecular interactions in meso-tetraphenylporphyrin diacid dimer (H4TPPCl2)2

Ding

et al. 2009

Phys. Chem. Chem. Phys.

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The intermolecular interactions between two meso-tetraphenylporphyrin diacid H(4)TPPCl(2) monomers are investigated by density functional theory with the PBE1PBE functional and 6-31G* basis set. Structures of five stable isomers of (H(4)TPPCl(2))(2) are determined. It is found that the interaction (IMHB-1) of Cl with ortho H atoms in two phenyl groups of H(4)TPPCl(2) is unique in that it is the strongest interaction between two H(4)TPPCl(2) monomers. Natural bond orbital analysis is carried out to explain the subtle differences of hydrogen bondings in these isomers. To understand the interactions of water molecule with H(4)TPPCl(2) and (H(4)TPPCl(2))(2), structures of H(4)TPPCl(2) x H(2)O and nine isomers of (H(4)TPPCl(2))(2) x H(2)O are also determined. The binding energy of H(4)TPPCl(2) x H(2)O is 36.47 kJ mol(-1), less than that of the most stable structure of (H(4)TPPCl(2))(2) dimers, 41.59 kJ mol(-1). The dimers containing the special IMHB-1 interactions may be the elementary building blocks for the aggregation of H(4)TPPCl(2), which is supported by the crystal structure of H(4)TPPCl(2).H(2)O x 2CH(3)CN. Thus, study of the interactions between two or a small number of gas molecules can provide important information for understanding the main interactions and stable structures in related condensed-phase systems.

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“…IHB are known to influence both conformational preferences and physico-chemical properties, which in turn influence bioactivities. [25][26][27][28][29][30][31][32][33][34][35][36] A study of the hypoxoside molecule with its two glucose moieties is computationally unaffordable; therefore, each glucose moiety was substituted with a methyl group, with the aim of reducing computational cost; this model structure will be denoted by the acronym HYP. As reported earlier by other researchers, it is very unlikely that the glucose moiety may have some influence on the reactivity of the systems, because the reactive site is universally accepted to be the phenolic ring.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Radical Scavenging Properties of Phenolic Pent-4-En-1-Yne Derivatives Isolated FromHypoxis Rooperi. A DFT Studyin vacuoand in Solution

Kabanda

Mammino

Murulana

et al. 2014

International Journal of Food Properties

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B3LYP/6-311+G * calculations were performed on five phenolic pent-4-en-1-yne derivatives, namely rooperol, dehydroxyrooperol I and II, bis-dehydroxyrooperol, and hypoxoside, to investigate and compare their antioxidant radical scavenging properties. The main objectives were to model, for the first time, the antioxidant properties of dehydroxyrooperol I and II and bis-dehydroxyrooperol, to clarify the possible role of hypoxoside as radical scavenger and to provide insight into molecular geometry factors influencing the radical scavenging properties of phenolic pent-4-en-1-yne derivatives. The study was conducted by checking the molecules' ability for two main antiradical mechanisms, hydrogen atom transfer and electron transfer. The results indicated that the antiradical properties of rooperol and the two dehydroxyrooperols are predominantly exerted through the hydrogen atom transfer mechanism and are the outcome of the stabilization of their neutral radical species through the interplay of hydrogen bond(s) and spin density distributions stabilizing their neutral radical species. The antiradical properties of bis-dehydroxyrooperol may be explained only in terms of the spin density distribution of its neutral radical species. The antiradical properties of hypoxoside, with O−H bond dissociation enthalpy considerably greater than that of phenol, could be considered to be minor and mainly governed by electron transfer mechanism.

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A computational study of the interactions of the caespitate molecule with water

Cited by 29 publications

References 48 publications

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

Theoretical study of intermolecular interactions in meso-tetraphenylporphyrin diacid dimer (H4TPPCl2)2

Antioxidant Radical Scavenging Properties of Phenolic Pent-4-En-1-Yne Derivatives Isolated FromHypoxis Rooperi. A DFT Studyin vacuoand in Solution

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