Noncovalent Interactions between Stacked Arenes in 1,8-Bis-(1-naphthyl)-naphthalenes

被引：4
|
作者：
Chiarucci, Michel [1 ]
Mazzanti, Andrea [2 ,3 ]
Righi, Paolo [2 ,3 ]
Bencivenni, Giorgio [2 ,3 ]
Mancinelli, Michele [2 ,3 ]
机构：
[1] Polycrystalline SpA, Via Cooperaz 29, I-40059 Medicina, Italy
[2] Univ Bologna, Dept Ind Chem Toso Montanari, Viale Risorgimento 4, I-40136 Bologna, Italy
[3] Univ Bologna, INSTM Res Unit Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 18期
关键词：
DFT calculations; Electronic circular dichroism; NMR spectroscopy; Noncovalent interactions;
D O I：
10.1002/ejoc.202100044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A number of 1,8-bis(1-naphthyl)-naphthalenes, bearing different substituents in the 1-naphthyl moieties have been prepared to investigate the noncovalent interactions between the stacked arenes. The best geometries were determined by means of DFT calculations, and experimentally checked by NMR and electronic circular dichroism (ECD). High temperature NMR spectroscopy allowed for the determination of the balance between dispersive and electrostatic contributions (ratio between two diastereomeric syn/anti isomers of compounds 1-6), while ECD analysis of the syn isomers of compounds 3-5 allowed for a deeper insight on the electrostatic contributions that drive the geometry between the interacting rings. The two rings preferentially adopt a parallel displaced geometry, whose interaction energy is strongly influenced by the electrostatic features of the two naphthyl rings, and that dispersive forces play a very minor role.
引用
收藏
页码：2594 / 2603
页数：10
相关论文
共 50 条
  • [31] 1,3-Bis{(+)-(S)-[1-(1-naphthyl)ethyl]iminomethyl}benzene dichloromethane solvate
    Espinosa Leija, Armando
    Hernandez, Guadalupe
    Cruz, Sandra
    Bernes, Sylvain
    Gutierrez, Rene
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1316 - U2188
  • [32] Crystal structure of 1,4-bis(1-naphthyl)-buta-1,3-diyne
    Manisekaran, T
    Sarkar, A
    Bhagwat, LP
    Talwar, SS
    Prasad, JS
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1995, 268 : 55 - 59
  • [33] Thermal Boundary Resistance between N,N′-Bis(1-naphthyl)-N,N′-diphenylbenzidine and Aluminum Films
    Oka, Nobuto
    Kato, Kazuki
    Yagi, Takashi
    Taketoshi, Naoyuki
    Baba, Tetsuya
    Shigesato, Yuzo
    JAPANESE JOURNAL OF APPLIED PHYSICS, 2011, 50 (11)
  • [34] Crystal structure of 1,4-bis(1-naphthyl)-buta-1,3-diyne
    Manisekaran, T.
    Sarkar, A.
    Bhagwat, L.P.
    Talwar, S.S.
    Prasad, J. Shashidhara
    Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 268
  • [35] STRUCTURE AND IR SPECTROSCOPIC BEHAVIOR OF 1,8-BIS-(DIMETHYLAMINO)NAPHTHALENE 2,4-DINITROIMIDAZOLATE
    GLOWIAK, T
    MALARSKI, Z
    SOBCZYK, L
    GRECH, E
    JOURNAL OF MOLECULAR STRUCTURE, 1987, 157 (04) : 329 - 337
  • [36] SYNTHESIS AND PROPERTIES OF 1,8-DI(2-THIENYL)NAPHTHALENES, 1,8-BIS(5,2'-BITHIOPHENE-2-YL)NAPHTHALENES, 1,8-BIS(5,2'/5',2''-TERTHIOPHENE-2-YL)NAPHTHALENES, AND 1,8-BIS(5,2'/5',2''/5'',2'''-QUATERTHIOPHENE-2-YL)NAPHTHALENES AND RELATED-COMPOUNDS
    KURODA, M
    NAKAYAMA, J
    HOSHINO, M
    FURUSHO, N
    KAWATA, T
    OHBA, S
    TETRAHEDRON, 1993, 49 (18) : 3735 - 3748
  • [37] Acid phosphates of 1-(1-naphthyl)ethylamine - Importance of symmetry relation between enantiomers
    Kaman, Ondrej
    Havlicek, David
    Cihelka, Jaroslav
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 : C481 - C481
  • [38] PERI-INTERACTIONS IN NAPHTHALENE DERIVATIVES - ROTATION IN 1,8-DISUBSTITUTED NAPHTHALENES
    ANDERSON, JE
    COOKSEY, CJ
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (23) : 942 - 943
  • [39] Competition Between π-π and C-H/π Interactions: A Comparison of the Structural and Electronic Properties of Alkoxy-Substituted 1,8-Bis((propyloxyphenyl)ethynyl)naphthalenes
    Carson, Bradley E.
    Parker, Trent M.
    Hohenstein, Edward G.
    Brizius, Glen L.
    Komorner, Whitney
    King, Rollin A.
    Collard, David M.
    Sherrill, C. David
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (52) : 19168 - 19175
  • [40] PERI-NAPHTHYLENEDIAMINES .6. NITRATION OF 1,8-BIS(DIALKYLAMINO)NAPHTHALENES
    KURASOV, LA
    POZHARSKII, AF
    KUZMENKO, VV
    KLYUEV, NA
    CHERNYSHEV, AI
    GORYAEV, SS
    CHIKINA, NL
    ZHURNAL ORGANICHESKOI KHIMII, 1983, 19 (03): : 590 - 597
12345