Citation: Kan Lei, Ma Ning, Wei Hao. Effect of Substituents on the Aggregation Behavior of 2-Ureido-4(1H)-pyrimidinone Derivatives[J]. Chemistry, ;2019, 82(4): 359-364, 349. shu

Effect of Substituents on the Aggregation Behavior of 2-Ureido-4(1H)-pyrimidinone Derivatives

Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education & College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001

Corresponding author: Wei Hao, weihao7512@126.com
Received Date: 19 October 2018
Accepted Date: 24 November 2018

Figures(5)

In this paper, UPy derivatives with different 6-position substituents and different isocyanate structures were prepared, and the effects of the 6-substituent and isocyanate structure on the formation and aggregation behavior of UPy dimers were studied. The 6-substituent on the UPy structure affects the density of the π-electron cloud. The dimer of ureidopyrimidone structure has the lowest potential energy, indicating that the structure is most stable in the system. With the increase of the electron-donating effect of the 6-substituent, the density of the π-electron cloud increased gradually, indicating a strong hydrogen bond. Due to the increase of the density of the π-electron cloud, the electron repulsion between the π bonds is enhanced, resulting in an increase of the (001) interplanar spacing in the derivative. The increase of the steric hindrance of the isocyanate structure hinders the π-π interaction between the pyrimidine rings, which will increase the (001) crystal plane spacing in the derivative.
- Ureido pyrimidone,
- Hydrogen bonding,
- Steric hindrance
1. [1]
  R P Sijbesma, F H Beijer, L Brunsveld et al. Science, 1997, 278(5343): 1601~1604.
2. [2]
  V Berl, M Schmutz, M J Krische et al. Chem. Eur. J., 2002, 8(5): 1227~1244.
3. [3]
  A W Bosman, H M Janssen, E W Meijer. Chem. Rev., 1999, 99(7): 1665~1688.
4. [4]
  K E Feldman, M J Kade, T F A de Greef et al. Macromolecules, 2008, 41(13): 4694~4700.
5. [5]
  M A Hossain, J M Llinares, D Powell et al. Inorg. Chem., 2001, 40(13): 2936~2937.
6. [6]
  D C Sherrington, K A Taskinen. Chem. Soc. Rev., 2001, 30(2): 83~93.
7. [7]
  L Brunsveld, B J B Folmer, E W Meijer et al. Chem. Rev., 2001, 101(12): 4071~4097.
8. [8]
  L Brunsveld, J Vekemans, J Hirschberg et al. PNAS, 2002, 99(8): 4977~4982.
9. [9]
  C Schmuck, W Wienand. Angew. Chem. Int. Ed., 2001, 40(23): 4363~4369.
10. [10]
  A Tessa ten Cate, R P Sijbesma. Macromol. Rapid. Commum., 2002, 23(18): 1094~1112.
11. [11]
  T F A de Greef, E W Meijer. Nature, 2008, 453(7192): 171~173.
12. [12]
  Y Chen, N Ballard, S A F Bon. Chem. Commun., 2013, 49(15): 1524~1526.
13. [13]
  S Hou, X Wang, S Park et al. Adv. Healthc. Mater., 2015, 4(10): 1491~1495.
14. [14]
  B Qin, S Zhang, Q Song et al. Angew. Chem. Int. Ed., 2017, 56(26): 7639~7643.
15. [15]
  F H Beijer, R P Sijbesma, H Kooijman et al. J. Am. Chem. Soc., 1998, 120(27): 6761~6769.
16. [16]
  H M Keizer, R P Sijbesma, E W Meijer. Eur. J. Org. Chem., 2004, (12): 2553~2555.
17. [17]
  J Elguero, C Marzin, A R Katritzky et al. Advances in Heterocyclic Chemistry, the Tautomerism of Heterocycles. New York: Academic Press, 1976.
1. [1]
  Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
2. [2]
  Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)₂]²⁺ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
3. [3]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
4. [4]
  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
5. [5]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
6. [6]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
7. [7]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
8. [8]
  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
9. [9]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
10. [10]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
11. [11]
  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
12. [12]
  Yang WANG , Xiaoqin ZHENG , Yang LIU , Kai ZHANG , Jiahui KOU , Linbing SUN . Mn single-atom catalysts based on confined space: Fabrication and the electrocatalytic oxygen evolution reaction performance. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2175-2185. doi: 10.11862/CJIC.20240165
13. [13]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
14. [14]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
15. [15]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
16. [16]
  Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
17. [17]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
18. [18]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
19. [19]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
20. [20]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(2008)
HTML views(658)

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