Predicting nucleation of isonicotinamide from the solvent - solute interactions of isonicotinamide in common organic solvents

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dc.contributor.author Lynch, Mark B.
dc.contributor.author Lawrence, Simon E.
dc.contributor.author Nolan, Michael
dc.date.accessioned 2018-03-07T17:18:59Z
dc.date.available 2018-03-07T17:18:59Z
dc.date.issued 2018
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.issn 1089-5639
dc.identifier.uri http://hdl.handle.net/10468/5583
dc.identifier.doi 10.1021/acs.jpca.8b01342
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.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher American Chemical Society 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
dc.internal.authorcontactother Michael Nolan, Tyndall Theory Modelling & Design Centre, University College Cork, Cork, Ireland. +353-21-490-3000 Email: michael.nolan@tyndall.ie en
dc.internal.availability Full text available en
dc.check.info Access to this article is restricted until 12 months after publication by request of the publisher.
dc.check.date 2019-03-07
dc.date.updated 2018-03-07T17:03:47Z
dc.description.version Accepted Version en
dc.internal.rssid 428639430
dc.contributor.funder Science Foundation Ireland en
dc.description.status Peer reviewed en
dc.identifier.journaltitle The Journal of Physical Chemistry A en
dc.internal.copyrightchecked No en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress michael.nolan@tyndall.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en


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