Statistic-Driven Proton Transfer Affecting Nanoscopic Organization in an Ethylammonium Nitrate Ionic Liquid and 1,4-Diaminobutane Binary Mixture: A Steamy Pizza Model

Mariani, Alessandro; Bonomo, Matteo; Passerini, Stefano

doi:10.3390/sym11111425

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Statistic-Driven Proton Transfer Affecting Nanoscopic Organization in an Ethylammonium Nitrate Ionic Liquid and 1,4-Diaminobutane Binary Mixture: A Steamy Pizza Model

Alessandro Mariani

^1,2,3,*

Matteo Bonomo

^1,4

and

Stefano Passerini

^2,3,*

Department of Chemistry, La Sapienza University of Rome, piazzale Aldo Moro 5, 00185 Rome, Italy

Helmholtz Institute Ulm (HIU), Helmholtzstrasse 11, 89081 Ulm, Germany

Karlsruhe Institute of Technology (KIT), P.O. Box 3640, 76021 Karlsruhe, Germany

⁴

Department of Chemistry and NIS Interdepartmental Centre and INSTM Reference Centre, University of Turin, via Pietro Giuria 7, 10125 Turin, Italy

Authors to whom correspondence should be addressed.

Symmetry 2019, 11(11), 1425; https://doi.org/10.3390/sym11111425

Received: 8 October 2019 / Revised: 13 November 2019 / Accepted: 15 November 2019 / Published: 19 November 2019

(This article belongs to the Special Issue Materials Science and X-Ray Diffraction)

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Abstract

Herein, we report on the theoretical and experimental investigation of the chemical equilibrium in a Ethylammonium Nitrate (EAN)/1,4-Diaminobutane (DAB) binary mixture displaying a significant excess of the latter component (namely, a 1:9 mole ratio). Both the neutral compounds, i.e., ethylamine (EtNH₂) and DAB, present very similar chemical properties, especially concerning their basic strength, resulting in a continuous jump of the proton from the ethylammonium to the diamine (and vice-versa). Due to the significant excess of DAB, the proton is (statistically) expected to be bound to one of its nitrogen atoms, leading to the formation of a new (ternary) mixture containing DAB (ca. 80%), ethylamine (ca. 10%) and 4-amino-1-butylammonium nitrate (ABAN, ca. 10%). This is probed by means of SAXS measurements, showing LqE (low q excess) that increases over time. This feature tends to stabilize after approximately one day. When the measurement is repeated after one year, the LqE feature shows an increased intensity. Based on the results of our simulations, we suggest that this phenomenon is likely due to partial ethylamine evaporation, pushing the equilibrium toward the formation of ABAN. View Full-Text

Keywords: Ionic liquids; binary mixtures; proton transfer; SAXS; molecular dynamics

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Mariani, A.; Bonomo, M.; Passerini, S. Statistic-Driven Proton Transfer Affecting Nanoscopic Organization in an Ethylammonium Nitrate Ionic Liquid and 1,4-Diaminobutane Binary Mixture: A Steamy Pizza Model. Symmetry 2019, 11, 1425. https://doi.org/10.3390/sym11111425

AMA Style

Mariani A, Bonomo M, Passerini S. Statistic-Driven Proton Transfer Affecting Nanoscopic Organization in an Ethylammonium Nitrate Ionic Liquid and 1,4-Diaminobutane Binary Mixture: A Steamy Pizza Model. Symmetry. 2019; 11(11):1425. https://doi.org/10.3390/sym11111425

Chicago/Turabian Style

Mariani, Alessandro, Matteo Bonomo, and Stefano Passerini. 2019. "Statistic-Driven Proton Transfer Affecting Nanoscopic Organization in an Ethylammonium Nitrate Ionic Liquid and 1,4-Diaminobutane Binary Mixture: A Steamy Pizza Model" Symmetry 11, no. 11: 1425. https://doi.org/10.3390/sym11111425

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Statistic-Driven Proton Transfer Affecting Nanoscopic Organization in an Ethylammonium Nitrate Ionic Liquid and 1,4-Diaminobutane Binary Mixture: A Steamy Pizza Model

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