C-H⋯X hydrogen bonds of acetylene, ethylene, and ethane with first - and second row hydrides

Journal of Physical Chemistry A

Volumn 105, Issue 18, 2001, Pages 4470-4479

  Hartmann, Michael ^a   Wetmore, Stacey D ^b   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PROTON DONORS;

ACETYLENE; BINDING ENERGY; ERRORS; ETHANE; ETHYLENE; HYDRIDES; MOLECULAR STRUCTURE; OPTIMIZATION; PROTONS;

HYDROGEN BONDS;

EID: 0035837964     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp001672e     Document Type: Article

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163. Reference values were taken from the compilation of best available ZPVEs reported by Martin, J. M. L.; de Oliveira, G. J. Chem. Phys. 1999, 7/7, 1843-1856. Consistent with this work, the reference value for the ZPVE for ethane was obtained from the B3-LYP/cc-pVTZ vibrational frequencies using a scale factor of 0.985.
164. 4 complex. We previously found negligible differences between the CCSD(T)/6-31 l+G(2df,2p) and CCSD-(T)/6-311+G(3df,2p) geometries for the acetylene-ammonia complex,7 whereas the smaller basis set leads to a substantial saving in computer time.
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183. See, for example, (a) van Lenthe, J. H.; van Duijneveldt-van de Rijdt, J. G. C. M.; van Duijneveldt, F. B. Adv. Chem. Phys. 1987,69,521-566.
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190. 3 (e) complexes (1.3, 0.5, 0.6, and 0.7 kj mol'1, respectively).
191. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 700,16 502-16 513.
192. The maximum lengthening of the intramolecular bond between the acceptor X and hydrogen in these cases is 0.001 Å. The corresponding ∠HXH angles are widened by up to 0.5° or diminished by up to 0.2°.
193. For this comparison, several different sets of van der Waals radii were chosen: (a) Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, New York, 1960; p 260.
194. (b) Bondi, A. J. Phys. Chem. 1964, 68,441-451.
195. (c) Allinger, N. L. Adv. Phys. Org. Chem. 1976,13, 2-82.
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198. In the absence of experimental evidence for the 'exact' position of the hydrogen atom between C and X, the C⋯X separation is often used as a geometrical criterion for the existence of C-H⋯X hydrogen bonds (see ref 4).
199. Schuster, P. Theor. Chim. Acta. 1970, 79, 212-224.
200. (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin Heidelberg, 1994; pp 29-32.
201. (b) Steiner, T. J. Chem. Soc., Chem. Commun. 1999, 313-314.
202. s symmetry) with water acting as the proton donor and involving an O-H⋯π rather than a C-H⋯O interaction was found to be slightly less stable than the nonplanar hydrogen-bonded complex by 3.4 kj mor1 on the BSSE-corrected CCSD(T)/6-311-f G(3df,2p)//MP2/ 6-31 l+G(3df,2p) surface. The intermolecular contact distance between the donor hydrogen and the midpoint of the acetylenic triple bond is calculated to be 2.334 Å. The conversion of the O-H⋯π complex to the C-H⋯O complex is determined to be almost barrierless. These results are in accord with the very flat potential surface in this region (see also refs 11 and 15).
203. -1) at the CCSD(T)/6-31 l+G(3df,2p)//MP2/6-31 l+G(3df,2p) level than the planar Cirsymmetric arrangement (Figure Id).
204. Other examples where the inclusion of BSSE has led to modified global minima have also been presented in the literature. (See, for example: (a) Hobza, P.; Havlas, Z. Collect. Czech. Chem. Commun. 1998, 63, 1343-1354
205. (b) Sadlej, J.; Mazurek, P. J. Mot. Struct. 1995, 337, 129-138.) In fact, it has been shown that both the location of potential minima and the vibrational frequencies can be dependent on the inclusion of BSSE. (See, for example:
206. (c) Bouteiller, Y.; Behrouz, H. J. Chem. Phys. 1992, 96, 6033-6038.)
207. -1 below the nonplanar geometry. Due to the well-documented importance of BSSE corrections, we can feel confident that the BSSE-corrected geometries are more reliable (see also refs 14 and 15). For examples of improved agreement with experiment when the BSSE-corrected potential energy surface is considered, see (a) Hobza, P.; Bludsky, O.; Suhai, S. Phys. Chem. Chem. Phys. 1999, J, 3073-3078 and ref 56b.
208. -1 on the BSSE-corrected surface. The bond distance between the donor hydrogen and the midpoint of the acetylenic triple bond is calculated to be 2.115 A. The conversion of the C-H⋯F hydrogen-bonded complex into the T-shaped H-F⋯πT complex is found to be almost barrierless.
209. Lias, S. G.; Bartmess, J. E.; Liebman. J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data Suppl. I 1988, 17.
210. 2O, and HF, which correlate nicely with the proton affinities of the proton acceptor.
211. 23 On both the MP2/6-31 l+G(3df,2p) and the B3-LYP/6-31 l+G(3df,2p) surfaces, the conversion of the C-H⋯Cl hydrogen-bonded complex into the Cl-H⋯π complex is almost barrierless. Refined CCSD(T)/6-311+ G(3df,2p) energy calculations predict the transition structure to lie lower in energy than the C-H⋯Cl form, suggesting again a barrierless transformation to the Cl-H⋯π complex.
212. 24a The bond distance between the.donor hydrogen and the midpoint of the ethylenic double bond is calculated to be 2.376 Å, compared with an experimental value of 2.48 Å.
213. -1.
214. -1). However, both structures represent local minima on the B3-LYP surface.
215. 2⋯FH, are dominated by the displacement of hydrogen in the proton acceptor out of the molecular plane.
216. (a) Hobza, P.; Spirko, V.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. A 1998, 702, 2501-2504.
217. (b) Hobza, P.; Spirko, V.; Havlas, Z.; Buchhold, K.; Reimann, B.; Earth, H.-D.; Brutschy, B. Chem. Phys. Lett. 1999, 299, 180-186.
218. (c) Cubero, E.; Orozco, M.; Hobza, P.; Luque, F. J. J. Phys. Chem. A 1999,103, 6394-6401.
219. (d) Hobza, P.; Havlas, Z. Chem. Phys. Lett. 1999, 303, 447-452.