Home

Citation: ZHANG Min, ZHENG Yan-Ping, JIANG Xiao-Nan, WANG Chang-Sheng. Effect of Substituents on Hydrogen Bonding in Strength N—H…O=C Hydrogen Bond Trimers[J]. Acta Physico-Chimica Sinica, ;2010, 26(03): 735-739. doi: 10.3866/PKU.WHXB20100235 shu

Effect of Substituents on Hydrogen Bonding in Strength N—H…O=C Hydrogen Bond Trimers

1.
School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, Liaoning Province, P. R. China

Received Date: 15 August 2009
Available Online: 5 January 2010

Theoretical calculations on a series of N—H…O=C hydrogen bond trimers were carried out using the MP2 method. We investigated the effect of substituents in hydrogen bond donor molecules on their hydrogen bond strength. The calculated results show that electron donating groups shorten the H…O distance and strengthen the N—H…O=C hydrogen bond whereas electron withdrawing groups lengthen the H…O distance and weaken the N—H…O=C hydrogen bond. Natural bond orbital (NBO) analysis further indicates that a stronger hydrogen bond in N—H…O=C results in a larger positive charge for the H atomand a larger negative charge for the O atomin the N—H…O=C bond. Natural bond orbital analysis also indicates that a stronger hydrogen bond in N—H…O=C results in a more charge transfer between the hydrogen bond donor and acceptor molecules, and results in a stronger second-order interaction energy between the oxygen lone pair and the N—H antibonding orbital. Hydrogen bonds in the N—H…O=C molecules closer to the substituent will be affected more.
- Hydrogen bond trimer,
- Substituent,
- Hydrogen bond strength,
- Natural bond orbital analysis
1. [1]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
2. [2]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
3. [3]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
4. [4]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
5. [5]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
6. [6]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
7. [7]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H₂O₂合成：协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
8. [8]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
9. [9]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
10. [10]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
11. [11]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
12. [12]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
13. [13]
  Qiang Zhou , Pingping Zhu , Wei Shao , Wanqun Hu , Xuan Lei , Haiyang Yang . Innovative Experimental Teaching Design for 3D Printing High-Strength Hydrogel Experiments. University Chemistry, 2024, 39(6): 264-270. doi: 10.3866/PKU.DXHX202310064
14. [14]
  Jiaxuan Zuo , Kun Zhang , Jing Wang , Xifei Li . 锂离子电池Ni-Co-Mn基正极材料前驱体的形核调控及机制. Acta Physico-Chimica Sinica, 2025, 41(1): 2404042-. doi: 10.3866/PKU.WHXB202404042
15. [15]
  Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
16. [16]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
17. [17]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
18. [18]
  Ling Zhang , Jing Kang . Turn Waste into Valuable: Preparation of High-Strength Water-Based Adhesives from Polymethylmethacrylate Wastes: a Comprehensive Chemical Experiments. University Chemistry, 2024, 39(2): 221-226. doi: 10.3866/PKU.DXHX202306075
19. [19]
  Xingyuan Lu , Yutao Yao , Junjing Gu , Peifeng Su . Energy Decomposition Analysis and Its Application in the Many-Body Effect of Water Clusters. University Chemistry, 2025, 40(3): 100-107. doi: 10.12461/PKU.DXHX202405074
20. [20]
  Zhexue Lu , Ping Wu , Huihui Li , Libai Wen . 四“味”一体的无机及分析化学课程思政. University Chemistry, 2025, 40(6): 333-340. doi: 10.12461/PKU.DXHX202405196

Get Citation

PDF

XML

Metrics

PDF Downloads(1340)
Abstract views(2787)
HTML views(44)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return