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- W2331273228 abstract "Two modes of intermolecular interactions (halogen and π–π charge-transfer bonding) between bromo- or iododinitrobenzene (XDNB) and tetramethyl-p-phenylenediamine (TMPD) are compared. X-ray crystallography revealed that TMPD·XDNB cocrystals comprise alternating donors/acceptors stacks formed by π-bonded (cofacial) TMPD and XDNB molecules. These structures also show two-point (C–X···O–N) halogen bonding between XDNB molecules resulting in formation of (XDNB)2 dimers. In solutions, XDNB and TMPD molecules formed 1:1 complexes showing strong absorption bands near 550 nm which followed the same Mulliken correlation as the associates of TMPD with the (halogen-free) nitro- and cyanobenzenes. In accord with the experimental data, density functional theory calculations with the M062X functional showed that TMPD·XDNB associates formed via π–π charge-transfer bonding are more stable (by 6–12 kcal/mol) than their halogen-bonded analogues. If XDNB is replaced with iodo- or bromoperfluorinated benzenes, or TMPD is replaced with pyridine, the energy gap between the π–π and halogen-bonded associates decreased. The analysis of the molecular-orbital interactions and surface electrostatic potentials of the interacting species indicated that charge-transfer contributions represent a critical component which determines variations of the strength of halogen bonding in these systems." @default.
- W2331273228 created "2016-06-24" @default.
- W2331273228 creator A5065366700 @default.
- W2331273228 creator A5091859622 @default.
- W2331273228 date "2015-04-09" @default.
- W2331273228 modified "2023-09-23" @default.
- W2331273228 title "Interplay of Halogen and π–π Charge-Transfer Bondings in Intermolecular Associates of Bromo- or Iododinitrobenzene with Tetramethyl-<i>p</i>-phenylenediamine" @default.
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- W2331273228 doi "https://doi.org/10.1021/acs.jpca.5b01600" @default.
- W2331273228 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25825078" @default.
- W2331273228 hasPublicationYear "2015" @default.
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