Benzene bond distances

FIGURE 11 1 Bond distances and bond angles of benzene... 

Because the carbons that are singly bonded m one resonance form are doubly bonded m the other the resonance description is consistent with the observed carbon-carbon bond distances m benzene These distances not only are all identical but also are intermediate between typical single bond and double bond lengths... 

A large body of experimental evidence confirms that covalent bonds have characteristic distances depending on bond type. Carbon-carbon single and double bond lengths are around 1.54A and 1.32A, respectively, while partial double bond distances, e.g., in benzene, are about 1.40A. 

Buckminsterfullerene (Cm or Buckyball ) is structurally related to corannulene. In which molecule would you expect 7U-orbital overlap be more effective Explain. How many chemically unique carbons are there in C6o Measure CC bond distances. How many unique distances are there Is each benzene fully delocalized or is one resonance contributor more important than the other ... 

Examine the geometry of methylbenzyne. Measure carbon-earbon distances. Which 7C bonds are deloealized and whieh are localized Is there really a triple bond (Compare bond distance to triple bond in hexa-l,5-dien-3-yne and to partial double bonds in benzene). Are you able to draw a single Lewis structure whieh adequately represents the geometry of the molecule ... 

Three years ago it was pointed out2 that observed values of interatomic distances provide useful information regarding the electronic structures of molecules and especially regarding resonance between two or more valence bond structures. On the basis of the available information it was concluded that resonance between two or more structures leads to interatomic distances nearly as small Us the smallest of those for the individual structures. For example, in benzene each carbon-carbon bond resonates about equally between a single bond and a double bond (as given by the two Kekul6 structures) the observed carbon-carbon distance, 1.39 A., is much closer to the carbon-carbon double bond distance, 1.38 A., than to the shrgle bond distance, 1.54 A. 

The quantitative comparison of measured. To values and 5 values calculated for models A for mesitylene and hexamethylbenzene is given in Tables XII and XIII. With omission of the innermost maximum and minimum, the unreliable third minimum, and the very weak fifth maximum for each substance, the average values sa/s0 = 1.000 and 1.002, respectively, are found. These correspond to the interatomic distances C — = 1.54 0.01 A. and Car-Car = 1.39 A. in both substances, the 0 —Qa distance being equal to the single-bond distance in aliphatic compounds and the Car—distance to that in benzene to within the probable error of the determination. 

Values found for interatomic distances and bond angles in the thirteen hydrocarbons studied are given in Table XIV. The carbon-carbon singlebond distance is found to have the constant value 1.54 = = 0.02 A., being unaffected by the presence of an adjacent double bond or benzene nucleus (provided that it does not form part of a conjugated system). The carbon-carbon double-bond distance in allene and acetylene has the value 1.34 A. This is 0.04 A. less than that formerly given by the table of covalent radii, which has accordingly been revised. The effect of the revision on the bond distance-resonance curve is discussed. 

We might expect that in compounds exhibiting delocalization the bond distances would lie between the values gives in Table 1.5. This is certainly the case for benzene, since the carbon-carbon bond distance is 1.40 A, which is between the 1.48 A for an sp -sp C—C single bond and the 1.32 A of the sp -sp C=C double bond. ... 

The order of aromaticity of these compounds is benzene > thiophene > pyrrole > fiiran, as calculated by an aromaticity index based on bond-distance measurements. This index has been calculated for five- and six-membered monocyclic and bicyclic heterocycles Bird, C.W. Tetrahedron, 1985, 41, 1409 1986, 42, 89 1987, 43, 4725. 

The crystal of 2 OPr recrystallized from EtOH/H20 solution, and the mixed crystal of the same ethyl and propyl cinnamate derivatives (2 OEt and 2 OPr), on photoirradiation for 2h at room temperature with a 500 W super-high-pressure Hg lamp, afforded the highly strained tricyclic [2.2] paracyclophane (2 OEt-2 OPr-cyclo) crystal quantitatively (Maekawa et ai, 1991b). A crystal structure analysis was carried out of a single crystal of the complex of 2 OEt-2 OPr-cyclo with HFIP (recrystallization solvent) in a 1 2 molar ratio. Fig. 13 shows the molecular structure of 2 OEt-2 OPr-cyclo viewed along the phenylene planes. The short non-bonded distances and deformation of the benzene rings, as seen in Fig. 13, are common to those of [2.2] paracyclophanes, as previously reported (Hope et ai, 1972a,b). 

The ability of Sadlej basis sets [37] to provide reliable values of has been tested in a limited number of cases with encouraging results [11]. In the present work on benzene the Sadlej basis set yields theoretical estimates close to those obtained by Perrin et al. [16] and Kama et al. [17], but smaller than those reported by Augspurger and Dykstra [18]. The C-C bond distance retained in [18], however, is 1.397 A, compared to 1.395 Aused by us, see Refs. [38] and [40]. 

Halogen % -bonding to benzene ring i Distances to six ring carbons k Distances to two carbon atoms 1 Distance from Br to aromatic plane m C-Br - X angle... 

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