Electronically tuned molecular torsion balances via remote substituents: a stabilizing factor for S $$\cdots$$ O chalcogen bond
Structural Chemistry - Trang 1-7 - 2023
Tóm tắt
Noncovalent interactions have an impact on the properties of condensed phases, solutions, and crystals. These interactions can occur between groups within a molecule (intra-) or between molecules (inter-). The current report examines a series of molecular balances as a quantitative method for evaluating the electronic effects of electron-donating (ED) and electron-withdrawing (EW) substituents in the para-position. Additionally, the impact on the stabilization of the two isomers (open and closed) and the strength of the intramolecular interactions is discussed in the report. The relative stability of the geometrical isomers, as well as the enthalpy, Gibbs free energy, and entropy for all 24 structures are analyzed. It was noted that the stability of the structures was associated with the substituents and the nature of the conformer. A strong positive correlation was observed between the calculated relative enthalpies and total energies as with R2 = 0.96. The calculated ΔH ranges between − 13.77 and 5.74 kJ mol−1, substitution of ED resulted in ΔH < 0, and the most negative value observed for strong ED namely N(CH3)2. It is worth noting that substitution of EW resulted in positive values of ΔH except for F. The calculated highest occupied molecular orbital and lowest unoccupied molecular orbital are found in the ranges − 5.19 to − 6.78 eV and − 5.58 to − 6.16 eV for open and closed conformers, respectively. The preference for the folded state can be attributed to weak S
$$\cdots$$
O chalcogen interactions. The observed relationship between electronic effects and torsional and chalcogen bonding properties offers insights into designing and manipulating molecular systems with specific conformational preferences and noncovalent interactions that may have potential implications in the development of molecular switches, sensors, and materials with tailored properties.
Tài liệu tham khảo
Metrangolo P et al (2008) Halogen bonding in supramolecular chemistry. Angew Chem Int Ed 47(33):6114–6127
Mele A et al (2005) A halogen-bonding-based heteroditopic receptor for alkali metal halides. J Am Chem Soc 127(43):14972–14973
Metrangolo P, Resnati G (2001) Halogen bonding: a paradigm in supramolecular chemistry. Chem Eur J 7(12):2511–2519
Politzer P, Murray JS (2013) Halogen bonding: an interim discussion. ChemPhysChem 14(2):278–294
Bui TTT et al (2009) The nature of halogen⋅⋅⋅ halogen interactions: a model derived from experimental charge-density analysis. Angew Chem 121(21):3896–3899
Bauzá A et al (2013) Halogen bonding versus chalcogen and pnicogen bonding: a combined Cambridge structural database and theoretical study. CrystEngComm 15(16):3137–3144
Scheiner S (2013) The pnicogen bond: Its relation to hydrogen, halogen, and other noncovalent bonds. Acc Chem Res 46(2):280–288
Zahn S et al (2011) Pnicogen bonds: a new molecular linker? Chem Eur J 17(22):6034–6038
Bai M et al (2014) A donor–acceptor–donor structured organic conductor with S··· s chalcogen bonding. Cryst Growth Des 14(2):459–466
Brezgunova ME et al (2013) Chalcogen bonding: experimental and theoretical determinations from electron density analysis. Geometrical preferences driven by electrophilic–nucleophilic interactions. Cryst Growth Des 13(8):3283–3289
Wang W, Ji B, Zhang Y (2009) Chalcogen bond: a sister noncovalent bond to halogen bond. J Phys Chem A 113(28):8132–8135
Lu Y et al (2012) Halogen bonding for rational drug design and new drug discovery. Expert Opin Drug Discov 7(5):375–383
Costa PJ, Nunes R, Vila-Viçosa D (2019) Halogen bonding in halocarbon-protein complexes and computational tools for rational drug design. Expert Opin Drug Discov 14(8):805–820
Di J et al (2021) Surface local polarization induced by bismuth-oxygen vacancy pairs tuning non-covalent interaction for CO2 photoreduction. Adv Energy Mater 11(41):2102389
Peng Q et al (2022) Cationic Ru complexes anchored on POM via non-covalent interaction towards efficient transfer hydrogenation catalysis. Mol Catal 517
Geng L et al (2019) Instant hydrogel formation of terpyridine-based complexes triggered by DNA via non-covalent interaction. Nanoscale 11(9):4044–4052
Hu L et al (2010) Predicting the binding affinity of epitope-peptides with HLA-A* 0201 by encoding atom-pair non-covalent interaction information between receptor and ligands. Chem Biol Drug Des 75(6):597–606
Singh J, Kim H, Chi KW (2021) Non-covalent interaction-directed coordination-driven self-assembly of non-trivial supramolecular topologies. Chem Rec 21(3):574–593
Turro NJ (2002) From molecular chemistry to supramolecular chemistry to superdupermolecular chemistry. Controlling covalent bond formation through non-covalent and magnetic interactions. Chem Commun (20):2279–2292
Yan W et al (2021) Harnessing noncovalent interaction of chalcogen bond in organocatalysis: From the catalyst point of view. Green Synth Catal 2(4):329–336
Scheiner S (2013) Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds. Int J Quantum Chem 113(11):1609–1620
Lenardão EJ, Santi C, Sancineto L (2018) New frontiers in organoselenium compounds. Vol. 6330. Springer
Beno BR et al (2015) A survey of the role of noncovalent sulfur interactions in drug design. J Med Chem 58(11):4383–4438
Werz DB, Gleiter R, Rominger F (2002) Nanotube formation favored by chalcogen− chalcogen interactions. J Am Chem Soc 124(36):10638–10639
Wilming FM, Becker J, Schreiner PR (2021) Quantifying solvophobic effects in organic solvents using a hydrocarbon molecular balance. J Org Chem 87(3):1874–1878
Schümann JM et al (2020) Intramolecular London dispersion interactions do not cancel in solution. J Am Chem Soc 143(1):41–45
Pollice R et al (2017) Attenuation of London dispersion in dichloromethane solutions. J Am Chem Soc 139(37):13126–13140
Mati IK, Adam C, Cockroft SL (2013) Seeing through solvent effects using molecular balances. Chem Sci 4(10):3965–3972
Muchowska KB et al (2013) Electrostatic modulation of aromatic rings via explicit solvation of substituents. J Am Chem Soc 135(27):9976–9979
Dominelli-Whiteley N et al (2017) Strong short-range cooperativity in hydrogen-bond chains. Angew Chem 129(26):7766–7770
Raymo FM, Stoddart JF (1999) Interlocked macromolecules. Chem Rev 99(7):1643–1664
Orlandi M et al (2017) Parametrization of non-covalent interactions for transition state interrogation applied to asymmetric catalysis. J Am Chem Soc 139(20):6803–6806
Seguin TJ, Wheeler SE (2016) Stacking and electrostatic interactions drive the stereoselectivity of silylium-ion asymmetric counteranion-directed catalysis. Angew Chem Int Ed 55(51):15889–15893
McNeil AJ et al (2006) Conjugated polymers in an arene sandwich. J Am Chem Soc 128(38):12426–12427
Vacas T et al (2010) Role of aromatic rings in the molecular recognition of aminoglycoside antibiotics: implications for drug design. J Am Chem Soc 132(34):12074–12090
McGaughey GB, Gagné M, Rappé AK (1998) π-stacking interactions: alive and well in proteins. J Biol Chem 273(25):15458–15463
Becke AD (1996) Density‐functional thermochemistry. IV. A new dynamical correlation functional and implications for exact‐exchange mixing. J Chem Phys 104(3):1040–1046
Frisch MJ et al (2016) Gaussian 16 Rev. C.01. Wallingford, CT
Pascoe DJ, Ling KB, Cockroft SL (2017) The origin of chalcogen-bonding interactions. J Am Chem Soc 139(42):15160–15167
Gurbanov AV et al (2020) Resonance assisted chalcogen bonding as a new synthon in the design of dyes. Chem Eur J 26(65):14833–14837
Bredas J-L (2014) Mind the gap! Mater Horiz 1(1):17–19
Zanjanchi F, Beheshtian J (2019) Natural pigments in dye-sensitized solar cell (DSSC): a DFT-TDDFT study. J Iran Chem Soc 16:795–805
Mehta N et al (2021) CHAL336 benchmark set: how well do quantum-chemical methods describe chalcogen-bonding interactions? J Chem Theory Comput 17(5):2783–2806