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

[41] Iridium catalyzed acceptor/acceptor carbene insertion into N-H bonds in water
Ramakrishna, Kankanala
Sivasankar, Chinnappan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (11) : 2392 - 2396
[42] Development of well-defined copper(I) catalysts for the addition of O-H and N-H bonds across alkyne bonds
Gunnoe, T. Brent
Cundari, Thomas R.
Delp, Samuel A.
Uddin, Jamal
Pouy, Mark J.
Ramdeen, Vijay M.
Cochrane, Nikki A.
Sabat, Michal
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[43] Water effect on the bond dissociation energy of O-H and N-H bonds in phenol and aniline: The testing of simple molecular dynamics model
Michalik, Martin
Vaganek, Adam
Poliak, Peter
ACTA CHIMICA SLOVACA, 2014, 7 (02): : 123 - 128
[44] N,N′-Bis(isonicotinoyl)hydrazine dihydrate at 120 (2) K:: a three-dimensional framework built from N-H•••O,O-H•••O,O-H•••N and C-H•••O hydrogen bonds
Portilla, Jaime
Cobo, Justo
de la Torre, Jose M.
Low, John N.
Glidewell, Christopher
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O1687 - O1690
[45] Rhodium(II) catalyzed synthesis of macrocycles incorporating oxindole via O-H/N-H insertion reactions
Muthusamy, Sengodagounder
Karikalan, Thangaraju
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (45) : 9243 - 9256
[46] Chemoselective carbene insertion into the N-H bonds of NH3•H2O
Liu, Zhaohong
Yang, Yong
Song, Qingmin
Li, Linxuan
Zanoni, Giuseppe
Liu, Shaopeng
Xiang, Meng
Anderson, Edward A.
Bi, Xihe
NATURE COMMUNICATIONS, 2022, 13 (01)
[47] Semiempirical calculations of O-H N-H and C-H hydrogen-bonding interactions. A comparison with high quality ab initio calculations.
Dannenberg, JJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 150 - COMP
[48] ABINITIO STUDY OF SILYLENE INSERTION INTO O-H BONDS - STABILITY OF ZWITTERIONIC INTERMEDIATES
RAGHAVACHARI, K
CHANDRASEKHAR, J
FRISCH, MJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3779 - 3781
[49] Electrochemical Enabled Cascade Phosphorylation of N-H/O-H/S-H Bonds with P-H Compounds: An Efficient Access to P(O)-X Bonds
Wang, Ruige
Dong, Xiaojuan
Zhang, Yonghong
Wang, Bin
Xia, Yu
Abdukader, Ablimit
Xue, Fei
Jin, Weiwei
Liu, Chenjiang
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (60) : 14931 - 14935
[50] Characterization of O-H•••O interactions in linear and cyclic clusters of boric acid: An ab initio, DFT, QTAIM and NBO study
Esrafili, Mehdi D.
Alizadeh, Vahideh
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2011, 974 (1-3) : 66 - 75

← 1 2 3 4 5 →