Predicting nucleation of isonicotinamide from the solvent - solute interactions of isonicotinamide in common organic solvents
| dc.contributor.author | Lynch, Mark B. | |
| dc.contributor.author | Lawrence, Simon E. | |
| dc.contributor.author | Nolan, Michael | |
| dc.contributor.funder | Science Foundation Ireland | en |
| dc.date.accessioned | 2018-03-07T17:18:59Z | |
| dc.date.available | 2018-03-07T17:18:59Z | |
| dc.date.issued | 2018 | |
| dc.date.updated | 2018-03-07T17:03:47Z | |
| dc.description.abstract | The interactions of isonicotinamide (INA) with seven common solvents (acetic acid, acetonitrile, acetone, chloroform, ethyl acetate, and methanol) have been studied to examine solute – solvent effects on the nucleation of INA from these solvents. In a simple model of 1:1 solute – solvent interactions, the strongest INA – solvent interaction is with acetic acid (binding energy, ΔEbind = -64.05 kJ mol-1) and the weakest is with chloroform (ΔEbind = -24.85 kJ mol-1). This arises since acetic acid and INA form a hydrogen bonding motif containing two moderate strength N-H...O hydrogen bonds, while chloroform and INA have a single weak C-H...O hydrogen bond. Taking acetic acid, chloroform, and methanol, the solvents with strongest, weakest and intermediate strength INA – solvent binding energy, the solvation of INA was studied to compare to the 1:1 model. Acetic acid has the strongest binding energy (-872.24 kJ mol-1) and solvation energy (-341.20 kJ mol-1) with chloroform binding energy ( 517.72 kJ mol-1) and solvation energy ( 199.05 kJ mol-1). Methanol has intermediate binding energy ( 814.19 kJ mol-1) and solvation energies ( 320.81 kJ mol-1). These results further confirm the recent the findings which indicate that the key trends in solvent – solute interactions can be determined from a simple and efficient 1:1 dimer model and can be used to predict ease of nucleation with stronger binding energies correlating to slower, more difficult nucleation. A limit of this model is revealed by considering alcohol and acid solvents with longer alkyl chains. | en |
| dc.description.sponsorship | Science Foundation Ireland (High Performance Computing Cluster at Tyndall National Institute) | en |
| dc.description.status | Peer reviewed | en |
| dc.description.version | Accepted Version | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.citation | Lynch, M. B., Lawrence, S. E. and Nolan, M. (2018) 'Predicting nucleation of isonicotinamide from the solvent – solute interactions of isonicotinamide in common organic solvents', The Journal of Physical Chemistry A. [In Press] DOI: 10.1021/acs.jpca.8b01342 | en |
| dc.identifier.doi | 10.1021/acs.jpca.8b01342 | |
| dc.identifier.issn | 1089-5639 | |
| dc.identifier.journaltitle | The Journal of Physical Chemistry A | en |
| dc.identifier.uri | https://hdl.handle.net/10468/5583 | |
| dc.language.iso | en | en |
| dc.publisher | American Chemical Society | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ | en |
| dc.relation.uri | https://pubs.acs.org/doi/10.1021/acs.jpca.8b01342 | |
| dc.rights | Copyright © American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Physical Chemistry A, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.jpca.8b01342. | en |
| dc.subject | Isonicotinamide (INA) | en |
| dc.subject | Nucleation | en |
| dc.subject | Solvent-solute interactions | en |
| dc.title | Predicting nucleation of isonicotinamide from the solvent - solute interactions of isonicotinamide in common organic solvents | en |
| dc.type | Article (peer-reviewed) | en |
