scholarly journals Influence of Substituents in the Aromatic Ring on the Strength of Halogen Bonding in Iodobenzene Derivatives

2020 ◽  
Vol 20 (11) ◽  
pp. 7197-7210
Author(s):  
Maria V. Chernysheva ◽  
Margarita Bulatova ◽  
Xin Ding ◽  
Matti Haukka
Keyword(s):  
Aromatic Ring ◽  
Halogen Bonding ◽  
Influence Of Substituents

scholarly journals Synthesis and Properties of ortho-t-BuSO2C6H4-Substituted Iodonium Ylides

Crystals ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1085
Author(s):  
Tomohiro Kimura ◽  
Shohei Hamada ◽  
Takumi Furuta ◽  
Yoshiji Takemoto ◽  
Yusuke Kobayashi
Keyword(s):  
Crystal Structures ◽  
Aromatic Ring ◽  
Natural Bond Orbital ◽  
Halogen Bonding ◽  
Electron Withdrawing Group ◽  
Iodonium Ylides

Iodonium ylides have recently attracted much attention on account of their synthetic applications. However, only a limited number of reports concerning the properties and reactivity of iodonium ylides exist, which is partly due to their instability. In this study, we synthesized several iodonium ylides that bear both an electron-withdrawing group and an aromatic ring with an ortho-t-BuSO2 group. Based on the crystal structures of the synthesized iodonium ylides in combination with natural-bond-orbital (NBO) calculations, we estimated the strength of the intra- and intermolecular halogen-bonding interactions. In addition, we investigated the reactivity of the iodonium ylides under photoirradiation.

The X40x10 Halogen Bonding Benchmark Revisited: Surprising Importance of (n-1)d Subvalence Correlation

2017 ◽  
Author(s):  
Manoj Kumar Kesharwani ◽  
Nitai Sylvetsky ◽  
Debashree Manna ◽  
Jan M.L. Martin
Keyword(s):  
Dissociation Energy ◽  
Noncovalent Interactions ◽  
Halogen Bonding ◽  
Coupled Cluster ◽  
Dissociation Energies ◽  
Iodine Species ◽  
Explicitly Correlated ◽  
High Level ◽  
Cluster Methods ◽  
Small Separation

<p>We have re-evaluated the X40x10 benchmark for halogen bonding using conventional and explicitly correlated coupled cluster methods. For the aromatic dimers at small separation, improved CCSD(T)–MP2 “high-level corrections” (HLCs) cause substantial reductions in the dissociation energy. For the bromine and iodine species, (n-1)d subvalence correlation increases dissociation energies, and turns out to be more important for noncovalent interactions than is generally realized. As in previous studies, we find that the most efficient way to obtain HLCs is to combine (T) from conventional CCSD(T) calculations with explicitly correlated CCSD-F12–MP2-F12 differences.</p>

Photoreaction of N-butyl 3,4-dimethoxy-6-nitrobenzamide with butylamine. A model study for lysine-directed photoaffinity labelling

1987 ◽  
Vol 52 (7) ◽  
pp. 1780-1785 ◽  
Author(s):  
Petr Kuzmič ◽  
Libuše Pavlíčková ◽  
Milan Souček
Keyword(s):  
Nitro Group ◽  
Aromatic Ring ◽  
Ultraviolet Irradiation ◽  
Title Compound ◽  
Reductive Coupling ◽  
Photoaffinity Labelling ◽  
Photolysis Rate ◽  
Model Study ◽  
A Minor

Ultraviolet irradiation of the title compound I in the presence of butylamine gave predominantly products of nucleophilic photosubstitution by the amine, i.e., nitroanilines IIa and IIb. Besides, small amounts of products of hydrolysis (phenol III) and reductive coupling (azoxybenzene IV) were also formed. Comparison of the overall photolysis rate of I with that of 3,4-dimethoxy-1-nitrobenzene (V) indicates a minor loss of reactivity, most probably due to some deviation from coplanarity of the activating nitro group and the aromatic ring.

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