Intramolecular Noncovalent Carbon Bonding Interaction Stabilizes the<i>cis</i>Conformation in Acylhydrazones

Naseer, Muhammad Moazzam; Hussain, Majid; Bauzá, Antonio; Lo, Kong Mun; Frontera, Antonio

doi:10.1002/cplu.201800329

Cited by 20 publications

(13 citation statements)

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A tetrel bond [103] was defined as a noncovalent bond between any electron donating moiety and a LA atom belonging to Group 14 of elements. The initial investigations were basically theoretical; [104][105][106][107][108][109][110] however, experimental research on TrB has rapidly grown in the last decade. Actually, there are plenty of examples in the literature reporting experimental [111,112] investigations on tetrel bonding, which was named as such in 2013 [113][114][115][116].…”

Section: Tetrel Bondsmentioning

confidence: 99%

Not Only Hydrogen Bonds: Other Noncovalent Interactions

2020

Self Cite

View full text Add to dashboard Cite

In this review, we provide a consistent description of noncovalent interactions, covering most groups of the Periodic Table. Different types of bonds are discussed using their trivial names. Moreover, the new name “Spodium bonds” is proposed for group 12 since noncovalent interactions involving this group of elements as electron acceptors have not yet been named. Excluding hydrogen bonds, the following noncovalent interactions will be discussed: alkali, alkaline earth, regium, spodium, triel, tetrel, pnictogen, chalcogen, halogen, and aerogen, which almost covers the Periodic Table entirely. Other interactions, such as orthogonal interactions and π-π stacking, will also be considered. Research and applications of σ-hole and π-hole interactions involving the p-block element is growing exponentially. The important applications include supramolecular chemistry, crystal engineering, catalysis, enzymatic chemistry molecular machines, membrane ion transport, etc. Despite the fact that this review is not intended to be comprehensive, a number of representative works for each type of interaction is provided. The possibility of modeling the dissociation energies of the complexes using different models (HSAB, ECW, Alkorta-Legon) was analyzed. Finally, the extension of Cahn-Ingold-Prelog priority rules to noncovalent is proposed.

show abstract

Section: Tetrel Bondsmentioning

confidence: 99%

Not Only Hydrogen Bonds: Other Noncovalent Interactions

2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…As examples, understanding the forces behind crystal engineering and supramolecular chemistry benefits from a knowledge of σ-hole interactions due to their directionality, strength, and selforganization properties which promote formation of adducts in the solid state [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][52]. The importance of σ-hole bonding has also been verified in the context of anion recognition processes [53][54][55][56][57][58][59][60][61], materials chemistry [62][63][64][65][66][67][68][69][70][71][72], or biochemistry [73][74][75][76][77][78][79][80][81]. An early work connecti...…”

Section: Introductionmentioning

confidence: 99%

Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

2021

View full text Add to dashboard Cite

Over the last years, scientific interest in noncovalent interactions based on the presence of electron-depleted regions called σ-holes or π-holes has markedly accelerated. Their high directionality and strength, comparable to hydrogen bonds, has been documented in many fields of modern chemistry. The current review gathers and digests recent results concerning these bonds, with a focus on those systems where both σ and π-holes are present on the same molecule. The underlying principles guiding the bonding in both sorts of interactions are discussed, and the trends that emerge from recent work offer a guide as to how one might design systems that allow multiple noncovalent bonds to occur simultaneously, or that prefer one bond type over another.

show abstract

“…In the solid state packing, the amide moiety in both benzoimidazole‐based hydrazones 5a and 5b adopt cis‐conformation, providing the possibility of appearance of a centrosymmetric amide dimer

R_{2}^{2} ((), 8)

{···H–N–C=O} 2 synthon. However, this dimeric synthon appeared in only compound 5a [(N(3)‐H(3)···O(1) 2.088 Å], facilitated by centrosymmetric CH···O interactions [(C(17)‐H(17C)···O(1) 2.353 Å] (Figure a) .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Rafiq

Khalid

Tahir

et al. 2019

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C 23 H 18 F 2 N 4 O (5a) and C 25 H 22 FN 5 O 3 (5b). Both 5a and 5b were synthesized and resolved into their crystal structures using SC-XRD for the assessment of bond lengths, bond angles, unit cells and space groups. The structures of 5a and 5b were chemically characterized using infrared (FT-IR), UV-Visible, nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR), EIMS and elemental analysis. DFT at M06-2X/6-31G(d,p) level of theory was performed to get optimized structures and countercheck the experimental findings. Overall, DFT findings show excellent concurrence with the experimental data which confirms the purity of both compounds. FMO, NBO analysis, MEP surfaces and nonlinear optical (NLO) properties were explored at same level of theory. UV-Vis analysis at TDDFT/M06-2X/6-31G(d,p) level of theory showed that 5b is red shifted with λ max 331.69 nm as compared to 5a with λ max 240.25 nm. Global reactivity parameters were estimated using energy of FMOs indicated the greater harness value than the softness values of 5a and 5b. NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper conjugative interactions are pivotal cause for the existence of 5a and 5b in the solid-state. NLO results of 5a and 5b were observed better than standard molecule recommended the NLO activity of said molecules for optoelectronic applications. Highlights• Two novel benzoimidazole-based hydrazones were synthesized.• XRD, NMR, FT-IR, UV-Vis, EIMS and elemental analysis were performed for the characterization.

show abstract

Intramolecular Noncovalent Carbon Bonding Interaction Stabilizes thecisConformation in Acylhydrazones

Cited by 20 publications

References 66 publications

Not Only Hydrogen Bonds: Other Noncovalent Interactions

Not Only Hydrogen Bonds: Other Noncovalent Interactions

Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Contact Info

Product

Resources

About