Mutual Relations between Substituent Effect, Hydrogen Bonding, and Aromaticity in Adenine-Uracil and Adenine-Adenine Base Pairs

Wieczorkiewicz, Paweł A.; Szatyłowicz, Halina; Krygowski, Tadeusz M.

doi:10.3390/molecules25163688

Cited by 6 publications

(4 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…16 Following Hammett's principle, the two σ components, i.e., the field/inductive constants and the resonance constants, were numerically quantified by means of F and R parameters, respectively. 17,18 The substituent effect has an important role in shaping various chemical and physical properties of chemical species, such as reactivity; 19−25 however, in regard to our present work, it also influences the potential for the formation of noncovalent bonds, including hydrogen bonding 26,27 and halogen bonding, 28 as well as also other nonspecific interactions. 29 The present paper studies salicylaldehyde hydrazones formed by the reaction of a modified salicylaldehyde with a primary amine, that is, hydrazine.…”

Section: ■ Introductionmentioning

confidence: 81%

“…Although Hammett’s equation has an empirical foundation, a theoretical methodology for substituent constant estimation has also been successfully implemented . Following Hammett’s principle, the two σ components, i.e., the field/inductive constants and the resonance constants, were numerically quantified by means of F and R parameters, respectively. , The substituent effect has an important role in shaping various chemical and physical properties of chemical species, such as reactivity; − however, in regard to our present work, it also influences the potential for the formation of noncovalent bonds, including hydrogen bonding , and halogen bonding, as well as also other nonspecific interactions …”

Section: Introductionmentioning

confidence: 98%

See 1 more Smart Citation

Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives

et al. 2023

View full text Add to dashboard Cite

The present study investigates the effect of the substitution of salicylaldehyde hydrazones at two selected positions, i.e., the para-position with regard to the proton-donating and proton-accepting centers forming the hydrogen bridge. A detailed analysis of structural data obtained by theoretical approaches and X-ray experiments, together with original resonance Hammett's constants, indicates that the strength of the intramolecular hydrogen bonding present in salicylaldehyde hydrazones can be selectively modulated by substitution of the parent molecular system with the chemical group of known π-electron-donating or -accepting properties. Our findings provide an insight into planning synthesis pathways for salicylaldehyde hydrazone species and predicting their result with regard to their H-bonding and related physical and chemical properties.

show abstract

Section: ■ Introductionmentioning

confidence: 81%

Section: Introductionmentioning

confidence: 98%

Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives

et al. 2023

View full text Add to dashboard Cite

show abstract

“…The contributions in this Special Issue can be grouped into three thematic areas: (i) specific properties of selected interactions evaluated for bi- or trimolecular complexes, [ 3 , 4 , 5 , 6 ] (ii) their role in the crystal packing [ 7 , 8 ], chemical [ 9 , 10 ] and enzymatic [ 11 ] reactions as well as (iii) manifestations of competing noncovalent interactions in solution [ 12 ] and into porous materials [ 13 ].…”

mentioning

confidence: 99%

“…The paper by Szatylowicz et al [ 4 ] describes the effect of substituents on the energy of specific noncovalent interactions in adenine-based bimolecular complexes and the aromaticity of the partners. Understanding these effects is essential for effective control of acid-base interactions in biochemistry, where stronger does not always mean better.…”

mentioning

confidence: 99%

Editorial to the Special Issue “Gulliver in the Country of Lilliput: An Interplay of Noncovalent Interactions”

Shenderovich

2020

Molecules

View full text Add to dashboard Cite

show abstract

Quantification of hydrogen bond energy based on equations using spectroscopic, structural, QTAIM-based, and NBO-based descriptors which calibrated by the molecular tailoring approach

Afonin,

Rusinska-Roszak

2023

J Mol Model

View full text Add to dashboard Cite

Context Hydrogen bonds critically influence the structure and properties of both organic molecules and biomolecules, as well as supramolecular assemblies. For this reason, the development and elaboration of methods for quantitative assessment of hydrogen bond energy is an urgent challenge. In this study, using a large series of hydroxycarbonyl aliphatic compounds with the O‒H···O = C intramolecular hydrogen bond, a bank of hydrogen bond descriptors was created, including spectroscopic, structural, QTAIM-based, and NBO-based parameters. It was shown that the O‒H vibration frequency, OH chemical shift as the spectroscopic descriptors, the O···H hydrogen bond length, O···O distance, and O‒H covalent bond length as the structural descriptors, the electron density and its Laplacian, electron potential energy density in the hydrogen bond critical point, the electron density at the ring critical point as the QTAIM-based descriptors change in a correlated manner. The same correlation is found in change of the charge transfer energy through a hydrogen bond, the occupancy of the O‒H bond antibonding orbital, the Wiberg indices of the O···H hydrogen bond, and the O‒H covalent bond, as well as the polarization of the O‒H bond, which are the NBO-based descriptors. It was also recognized that the specified descriptors from the spectroscopic, structural, QTAIM-based, and NBO-based categories are functionally related to the values of intramolecular hydrogen bond energy, quantified via the molecular tailoring approach. This allowed one to obtain a system of equations for quantitative estimation of intramolecular hydrogen bond energy based on the spectroscopic, structural, QTAIM, and NBO descriptors, which makes such quantification more dependable and reliable. Methods To obtain the spectroscopic descriptors, the vibrational spectra and shielding constants were calculated using the GIAO method. Structural descriptors were obtained for the equilibrium geometry of molecules, calculated at the MP2(FC)/6–311 + + (2d,2p) level using the Gaussian 09 program. The QTAIM-based descriptors were calculated using the AIMAll program within the framework of the quantum theory “Atoms in Molecules.” The NBO-based descriptors were calculated using the NBO 3.1 program implemented into Gaussian 09. To quantify the energy of intramolecular hydrogen bonds, molecular fragmentation was used within the molecular tailoring approach.

show abstract

Mutual Relations between Substituent Effect, Hydrogen Bonding, and Aromaticity in Adenine-Uracil and Adenine-Adenine Base Pairs

Cited by 6 publications

References 61 publications

Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives

Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives

Editorial to the Special Issue “Gulliver in the Country of Lilliput: An Interplay of Noncovalent Interactions”

Quantification of hydrogen bond energy based on equations using spectroscopic, structural, QTAIM-based, and NBO-based descriptors which calibrated by the molecular tailoring approach

Contact Info

Product

Resources

About