Singlet Methylene Insertion Into Polar O-H and N-H Bonds of Water and Ammonia-Ab Initio and DFT Study

被引：1

作者：

Ramasami, K. ^{[2
]}

Ramalingam, M. ^{[1
]}

Venuvanalingam, P. ^{[3
]}

Jaccob, M. ^{[3
]}

机构：

[1] PRIST Univ, CRD, Thanjavur 613403, India

[2] Nehru Mem Coll, Dept Chem, Puthanampatti 621007, India

[3] Bharathidasan Univ, Sch Chem, Tiruchirappalli 620024, India

来源：

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY | 2010年 / 110卷 / 07期

关键词：

methylene; ab initio; DFT; QCISD; QCISD (T); O-H insertion; N-H insertion; DENSITY-FUNCTIONAL THERMOCHEMISTRY; CHLOROCARBENES INSERTIONS; TRIPLET SEPARATION; MOLLER-PLESSET; CH2; YLIDES;

D O I：

10.1002/qua.22236

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Correlated ab initio molecular orbital, OFT, QCISD, G3MP2, and QCISD(T) calculations have been used to investigate the geometries, energetics, and mechanisms governing the insertion reactions of (CH2)-C-1 into O-H and N-H bonds of water and ammonia, respectively, in gas phase adopting 6-311+ +g(d, p) basis set. It is found that (CH2)-C-1 reacts with water and ammonia to produce the ylide-like intermediates H2C-OH2 and H2C-NH3, which in turn undergo 1,2-hydrogen shift to produce methanol and methylamine, respectively. Results obtained indicate that in the gas phase, the ylides and the transition states are located below the reactants' energy levels. (C) 2009 Wiley Periodicals, Inc. Int J Quantum Chem 110: 1310-1316, 2010

引用

页码：1310 / 1316

页数：7

共 50 条

[31] Intramolecular interactions (O-H∙∙∙O, C-H∙∙∙N, N-H∙∙∙π) in isomers of neutral, cation, and anion dopamine molecules: A DFT study on the influence of solvents (water and ethanol)
Thekkayil Sangeetha
Senthilkumar Lakshmipathi
Journal of Molecular Modeling, 2023, 29
[32] AB-INITIO MOLECULAR-ORBITAL STUDY OF THE MECHANISM OF H-H, C-H, N-H, O-H, AND SI-H BOND ACTIVATION ON TRANSIENT CYCLOPENTADIENYLCARBONYLRHODIUM
MUSAEV, DG
MOROKUMA, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) : 799 - 805
[33] Investigating the oxidative additions of O-H and N-H bonds to geometrically distorted phosphorus (III) compounds
McCarthy, Sean
Radosevich, Alexander
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
[34] Niobium-Catalyzed Intramolecular Addition of O-H and N-H Bonds to Alkenes: A Tool for Hydrofunctionalization
Ferrand, Laura
Tang, Yue
Aubert, Corinne
Fensterbank, Louis
Mouries-Mansuy, Virginie
Petit, Marc
Amatore, Muriel
ORGANIC LETTERS, 2017, 19 (08) : 2062 - 2065
[35] The shielding constants and scalar couplings in N-H•••O=C and N-H•••N=C hydrogen bonded systems:: An ab initio MO study
Pecul, M
Leszczynski, J
Sadlej, J
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (34): : 8105 - 8113
[36] Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds
Burtoloso, Antonio C. B.
Santiago, Joao V.
Bernardim, Barbara
Talero, Alexander G.
CURRENT ORGANIC SYNTHESIS, 2015, 12 (05) : 650 - 659
[37] 3-Nitrobenzaldehyde isonicotinoylhydrazone monohydrate redetermined at 120 K:: sheets built from O-H • • • O, O-H • • • N, N-H • • • O and C-H • • • O hydrogen bonds
Wardell, Solange M. S. V.
Wardell, James L.
Low, John N.
Glidewell, Christopher
de Souza, Marcus V. N.
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 (o42-o44): : O42 - O44
[38] Identity proton-transfer reactions from C-H, N-H, and O-H acids. An ab initio, DFT, and CPCM-B3LYP aqueous solvent model study
Gronert, S. (sgronert@sfsu.edu), 1600, American Chemical Society (125):
[39] Cooperative influence of water binding to peptides by N-H•••OH2 and C=O•••HOH hydrogen bonds: Study by Ab Initio calculations
Sun, Chang-Liang
Wang, Chang-Sheng
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2012, 112 (10) : 2336 - 2341
[40] Identity proton-transfer reactions from C-H, N-H, and O-H acids. An ab initio, DFT, and CPCM-B3LYP aqueous solvent model study
Keeffe, JR
Gronert, S
Colvin, ME
Tran, NL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) : 11730 - 11745

← 1 2 3 4 5 →