Ionic Hydrogen and Halogen Bonding in the Gas Phase Association of Acetonitrile and Acetone with Halogenated Benzene Cations

2018 ◽  
Vol 123 (7) ◽  
pp. 1363-1371 ◽  
Author(s):  
Adam C. Pearcy ◽  
Kyle A. Mason ◽  
M. Samy El-Shall
Keyword(s):  
Gas Phase ◽  
Halogen Bonding

scholarly journals Corrigendum: Multiple Multidentate Halogen Bonding in Solution, in the Solid State, and in the (Calculated) Gas Phase

2015 ◽  
Vol 21 (44) ◽  
pp. 15467-15467
Author(s):  
Stefan H. Jungbauer ◽  
Severin Schindler ◽  
Eberhardt Herdtweck ◽  
Sandro Keller ◽  
Stefan M. Huber
Keyword(s):  
Solid State ◽  
Gas Phase ◽  
Halogen Bonding

Noncovalent Halogen Bonding as a Mechanism for Gas-Phase Clustering

2017 ◽  
Vol 28 (10) ◽  
pp. 2209-2216 ◽  
Author(s):  
Christina Wegeberg ◽  
William A. Donald ◽  
Christine J. McKenzie
Keyword(s):  
Gas Phase ◽  
Halogen Bonding

Multiple Multidentate Halogen Bonding in Solution, in the Solid State, and in the (Calculated) Gas Phase

2015 ◽  
Vol 21 (39) ◽  
pp. 13625-13636 ◽  
Author(s):  
Stefan H. Jungbauer ◽  
Severin Schindler ◽  
Eberhardt Herdtweck ◽  
Sandro Keller ◽  
Stefan M. Huber
Keyword(s):  
Solid State ◽  
Gas Phase ◽  
Halogen Bonding

Enthalpy and entropy factors in gas phase halogen bonding: compensation and competition

CrystEngComm ◽  
2013 ◽  
Vol 15 (16) ◽  
pp. 3145 ◽  
Author(s):  
Peter Politzer ◽  
Jane S. Murray
Keyword(s):  
Gas Phase ◽  
Halogen Bonding ◽  
Enthalpy And Entropy

scholarly journals “Anti-Electrostatic” Halogen Bonding

2020 ◽  
Author(s):  
Jana Holthoff ◽  
Elric Engelage ◽  
Robert Weiss ◽  
Stefan Huber
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Gas Phase ◽  
Electrostatic Potential ◽  
Lewis Acids ◽  
Halogen Bonding ◽  
Halide Complexes ◽  
Self Association ◽  
Solid State Structures ◽  
Van Der Waals Radii

Halogen bonding (XB) is often described as being driven predominantly by electrostatics, and thus adducts between <i>anionic</i> XB donors (halogen-based Lewis acids) and anions seem counter­intuitive. Such “anti-electrostatic” XBs have been predicted theoretically, but there are currently no experimental examples based on organic XB donors. Herein, we report the synthesis of two negatively charged organoiodine derivatives, which were subsequently investigated towards their ability to form “anti-electrostatic” XBs with anions. Even though the electrostatic potential is universally negative across the surface of both compounds, DFT calculations indicate kinetic stabilization of their halide complexes in the gas phase and particularly in solution. Experimentally, self-association of the anionic XB donors was observed in solid-state structures, resulting in dimers, trimers and infinite chains. In addition, co-crystals with halides were obtained which featured XB adducts between two or even three anions. The bond-lengths of all observed interactions are 14-21% shorter than sum of the van-der-Waals radii.

scholarly journals “Anti-Electrostatic” Halogen Bonding

2020 ◽  
Author(s):  
Jana Holthoff ◽  
Elric Engelage ◽  
Robert Weiss ◽  
Stefan Huber
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Gas Phase ◽  
Electrostatic Potential ◽  
Lewis Acids ◽  
Halogen Bonding ◽  
Halide Complexes ◽  
Self Association ◽  
Solid State Structures ◽  
Van Der Waals Radii

Halogen bonding (XB) is often described as being driven predominantly by electrostatics, and thus adducts between <i>anionic</i> XB donors (halogen-based Lewis acids) and anions seem counter­intuitive. Such “anti-electrostatic” XBs have been predicted theoretically, but there are currently no experimental examples based on organic XB donors. Herein, we report the synthesis of two negatively charged organoiodine derivatives, which were subsequently investigated towards their ability to form “anti-electrostatic” XBs with anions. Even though the electrostatic potential is universally negative across the surface of both compounds, DFT calculations indicate kinetic stabilization of their halide complexes in the gas phase and particularly in solution. Experimentally, self-association of the anionic XB donors was observed in solid-state structures, resulting in dimers, trimers and infinite chains. In addition, co-crystals with halides were obtained which featured XB adducts between two or even three anions. The bond-lengths of all observed interactions are 14-21% shorter than sum of the van-der-Waals radii.

Structure and energetics of gas phase halogen-bonding in mono-, bi-, and tri-dentate anion receptors as studied by BIRD

2013 ◽  
Vol 15 (20) ◽  
pp. 7638 ◽  
Author(s):  
Elizabeth A. L. Gillis ◽  
Maria Demireva ◽  
Mohammed G. Sarwar ◽  
Michael G. Chudzinski ◽  
Mark S. Taylor ◽  
...  
Keyword(s):  
Gas Phase ◽  
Halogen Bonding ◽  
Anion Receptors

Gas phase hydration of halogenated benzene cations. Is it hydrogen or halogen bonding?

2017 ◽  
Vol 19 (28) ◽  
pp. 18603-18611 ◽  
Author(s):  
Kyle A. Mason ◽  
Adam C. Pearcy ◽  
Isaac K. Attah ◽  
Sean P. Platt ◽  
Saadullah G. Aziz ◽  
...  
Keyword(s):  
Gas Phase ◽  
Halogen Bonding ◽  
Radical Cations ◽  
Halogen Bonds

The size of the σ-hole increases significantly in bromobenzene and iodobenzene radical cations leading to ionic halogen bonds with water.

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