Thermal motion of tert-butyl groups III. tert-Butyl substituents in aromatic hydrocarbons, the view from the bottom of the well

被引:1
|
作者
Frey, Joseph [2 ]
Khan, Saeed I. [1 ]
Knobler, Carolyn B. [1 ]
Lightner, David A. [3 ]
Maverick, Emily F. [1 ]
Phillips, Daniel J. [4 ]
Rappoport, Zvi [5 ]
Trueblood, Kenneth N. [1 ]
机构
[1] Univ Calif Los Angeles, Los Angeles, CA 90095 USA
[2] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel
[3] Univ Nevada, Reno, NV 89557 USA
[4] Bethany Coll, Bethany, WV 26032 USA
[5] Hebrew Univ Jerusalem, IL-91904 Jerusalem, Israel
来源
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE | 2010年 / 66卷
基金
美国国家科学基金会;
关键词
anisotropic displacement parameters; Hirshfeld test; rotation barriers; helicenes; aromaticity; ANISOTROPIC DISPLACEMENT PARAMETERS; X-RAY-DIFFRACTION; CAMBRIDGE STRUCTURAL DATABASE; PROTON SPIN RELAXATION; CRYSTAL-STRUCTURE; T-BUTYL; GROUP REORIENTATION; MOLECULAR-SOLIDS; ROTATION BARRIERS; TORSIONAL MOTION;
D O I
10.1107/S0108768110040024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rigidity of the tert-butyl group (TBG) as a substituent in aromatic hydrocarbons is investigated, with a modified Hirshfeld test of anisotropic displacement parameters (ADPs) as a primary criterion. Four new structures are analyzed, along with low-temperature studies of a previously published crowded supermesityl dimer; three of the five structures meet the primary test. Most of the TBGs meet the Hirshfeld test at 100 K, and the ADPs are improved by omitting low-order data in the final refinement. The three most precise structures yield a wide variation in libration amplitudes (and in estimated rotation barriers) for 13 unique TBGs. A similar range of values is found in analyses of structures in the Cambridge Crystallographic Database. The libration amplitudes are calculated with the program THMA14C, with each TBG as an attached rigid group (ARG). Packing analysis suggests that large ADPs, especially for some individual TBG methyl groups, correspond to voids in the crystal. Published barriers to TBG reorientation, determined by solid-state NMR spin-lattice relaxation methods, for six related crystalline compounds are compared with barriers calculated from their crystal structure data.
引用
收藏
页码:622 / 638
页数:17
相关论文
共 12 条
  • [1] The relationship between crystal structure and NMR relaxation in molecular solids with tert-butyl groups
    Rheingold, Arnold L.
    DiPasquale, Antonio G.
    Beckmann, Peter A.
    CHEMICAL PHYSICS, 2008, 345 (01) : 116 - 118
  • [2] Structure and thermal stability of cadmium arachidate/poly(tert-butyl methacrylate) alternating Langmuir-Blodgett film
    Cha, J
    See, YK
    Lee, J
    Chang, T
    SYNTHETIC METALS, 2001, 117 (1-3) : 149 - 152
  • [3] Thermal and Crystallographic Studies of tert-Butyl 2-amino-1H-1,3-benzodiazole-l-carboxylate
    Singh, Vishal
    Kant, Rama
    Agarwal, Alka
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES INDIA SECTION A-PHYSICAL SCIENCES, 2016, 86 (01) : 7 - 13
  • [4] A fast and practical synthesis of tert-butyl esters from 2-tert-butoxypyridine using boron trifluoride•diethyl etherate under mild conditions
    Minh Thanh La
    Kim, Hee-Kwon
    TETRAHEDRON, 2018, 74 (27) : 3748 - 3754
  • [5] STRUCTURE AND THERMAL PROPERTIES OF VOLATILE MIXED-LIGAND MAGNESIUM COMPLEXES: EFFECT OF TERT-BUTYL AND PHENYL SUBSTITUTES IN A FLUORINATED β-DIKETONATE
    Vikulova, E. S.
    Sukhikh, A. S.
    Mikhaylova, M. A.
    Nazarova, A. A.
    Zherikova, K., V
    Morozova, N. B.
    JOURNAL OF STRUCTURAL CHEMISTRY, 2022, 63 (08) : 1323 - 1332
  • [6] Ruthenium(III) unsymmetrical Schiff base complex supported on γ-Fe 2 O 3 magnetic nanoparticles: A new heterogeneous nanocatalyst for efficient oxidation of hydrocarbons with tert-butyl hydroperoxide
    Mohammadabadi, Zeynab
    Ardakani, Mehdi Hatefi
    Naeimi, Atena
    INORGANIC CHEMISTRY COMMUNICATIONS, 2024, 169
  • [7] Synthesis, structural characterization and bioactivities of iron(III) and copper(II) complexes containing Schiff base thiourea ligands of 5-(tert-butyl)-2-hydroxybenzaldehyde
    Trung, Nguyen Quang
    Nam, Pham Thi Phuong
    Tuyen, Nguyen Van
    VIETNAM JOURNAL OF CHEMISTRY, 2024, 62 : 8 - 14
  • [8] Low-temperature CVD of iron, cobalt, and nickel nitride thin films from bis[di(tert-butyl)amido]metal(II) precursors and ammonia
    Cloud, Andrew N.
    Davis, Luke M.
    Girolami, Gregory S.
    Abelson, John R.
    JOURNAL OF VACUUM SCIENCE & TECHNOLOGY A, 2014, 32 (02):
  • [9] Structural modification of graphene material by silicon mono-doping and codoping with heteroatoms as sensors for methyl tert-butyl ether (MTBE) as a fuel additive: Insights from DFT
    Gulack, Alpha O.
    Arikpo, Temple O.
    Benjamin, Innocent
    Ogbogu, Chisom E.
    Pembere, Anthony M. S.
    Louis, Hitler
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2024, 1239
  • [10] Synthesis, spectroscopy, electrochemistry, and methylation reaction of the dithiolate-based cobalt(II) complex derived from tert-butyl N-(2-mercaptoethyl)carbamate
    Ibrahim, Mohamed M.
    Mersal, Gaber A. M.
    El-Shafai, Nagi
    Youssef, Mohamed M.
    Shokry, Hanaa
    COMPTES RENDUS CHIMIE, 2014, 17 (10) : 1013 - 1022