Augmentation of inductive effects through short range intramolecular hydrogen bonds for the improvement of cooperativity of trimeric rosettes

Petelski, Andre Nicolai; Bundrea, Tamara; Peruchena, Nélida María

doi:10.1039/d4me00008k

Mol. Syst. Des. Eng.

2024

DOI: 10.1039/d4me00008k

|View full text |Cite

Augmentation of inductive effects through short range intramolecular hydrogen bonds for the improvement of cooperativity of trimeric rosettes

Andre Nicolai Petelski,

Tamara Bundrea,

Nélida María Peruchena

Abstract: Cooperativity in hydrogen bonds can be crucial for the stabilization of supramolecular systems. In this contribution we propose a simple covalent modification within a pyrazole-based trimeric rosette that significantly improves...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Probing Self‐Assembly of Ammeline in Chloroform and Aqueous Media: Interplay Between Hydrogen Bonding Diversity and Dimerization

Pamies,

Peruchena,

Petelski

2024

ChemPlusChem

View full text Add to dashboard Cite

Ammeline (AM) is a molecule with a very low reputation in the field of supramolecular community, but with a recently proven potential both experimentally and theoretically. In this work, dispersion‐corrected density functional theory (DFT‐D) computations and molecular dynamics (MD) simulations were employed to understand the aggregation mechanism of AM in chloroform and water media. Our DFT‐D and MD analyzes show that the most important interactions are those formed by the amine groups (−NH2) with both the pyridine‐type nitrogen atoms and the carbonyl groups (C=O). In the more polar solvent, the interactions between water molecules and the C=O group prevent the AM from forming more interactions with itself. Nevertheless, four types of dimers involving N−H∙∙∙O interactions were found to exist in water solutions. The overlooked tetrel bond between endocyclic N and C atoms can also stabilize dimers in solution. Moreover, while most AM dimers are enthalpy‐driven, our results indicate that the unique DD‐AA dimer (D=donor, A=acceptor) that originates cyclic rosettes is entropy‐driven.

show abstract

Probing Self‐Assembly of Ammeline in Chloroform and Aqueous Media: Interplay Between Hydrogen Bonding Diversity and Dimerization

Pamies,

Peruchena,

Petelski

2024

ChemPlusChem

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Augmentation of inductive effects through short range intramolecular hydrogen bonds for the improvement of cooperativity of trimeric rosettes

Abstract: Cooperativity in hydrogen bonds can be crucial for the stabilization of supramolecular systems. In this contribution we propose a simple covalent modification within a pyrazole-based trimeric rosette that significantly improves...

Cited by 1 publication

References 47 publications

Probing Self‐Assembly of Ammeline in Chloroform and Aqueous Media: Interplay Between Hydrogen Bonding Diversity and Dimerization

Probing Self‐Assembly of Ammeline in Chloroform and Aqueous Media: Interplay Between Hydrogen Bonding Diversity and Dimerization

Contact Info

Product

Resources

About