Silver phenylacetylide

To the best of our knowledge, PhC=CAg is the only other silver acetylide for which there is a measured enthalpy of formation. Indeed, it is the only other classical silver organometalhc compound for which the standard enthalpy of formation has become available in this century Using static-bomb combustion calorimetry, Bykova and her coworkers11 determined this value to be 346.3 2.0 kJ mol-1. 

It is not obvious how to ascertain the reasonableness of the previous two silver acetylide values because there seems to be insufficient data to make meaningful comparisons. Yet, using organic thermochemical data from Reference 12 for diphenylacetylene, the formal, organometalhc, solid phase disproportionation reaction 3 

Joel F. Liebman, Jose Martinho Simoes and Suzanne W. Slayden 

TABLE 2. Enthalpies of formation (AfHm ) and enthalpies of synthesis [Ar m equation 5] of disilver acetylide silver salt complexes (kJmol-1) 

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With the finding that silver phenylacetylide was soluble in pyridine, Agawa and coworkers attempted to react the acetylide with benzoyl chloride in pyridine as solvent. While the expected ynone was isolated in poor yield, the predominant product of reaction was from initial acylation of the pyridine nitrogen to produce the electrophilic pyridinium salt, followed by addition of the silver acetylide to the 2... 

The enthalpies of formation of AgCN and HCN were taken from Reference 6 and that of silver phenylacetylide from Reference 10. The requisite value for liquid phenylacetylene was found by either... 

FAB-MS of silver phenylacetylide complex 191 shows a fragmentation pattern involving loss of PPh3, Ph and PhC2 groups and intermediate formation of clusters of formula 192. It should be pointed out that 191 exists in the crystalline state as a disproportionation copolymer, analogous to 115 (item C-4 of Table 3)253. 

A -Benzoyloxypyridinium chloride (72), prepared from pyridine oxide and benzoyl chloride, reacts with silver phenylacetylide selectively at position 2 to afford 2-(phenylethynyl)pyridine (73). The bromine atom of the tetrahydro-l,4-oxazin-2-one 74 is replaced by an alkynyl group on treatment with stannanes 75 (R = hexyl or Ph) the products 76 are transformed into ( S)-amino acids 77 by catalytic hydrogenation. ... 

Silver chloroacetylide, 0566 Silver cyclopropylacetylide, 1838 Silver 1,3,5-hexatrienide, 2052 Silver 3-hydroxypropynide, 1088 Sodium acetylide, 1022 Sodium bromoacetylide, 0581 Sodium chloroacetylide, 0601 Sodium ethoxyacetylide, 1478 Sodium methoxyacetylide, 1123 Sodium phenylacetylide, 2911 Strontium acetylide, 1026 Tetraethynylgermanium, 2895 Tetraethynyltin, 2901 Thallium iodacetylide, 0984... 

Silver chloroacetylide, 0563 Silver cyclopropylacetylide, 1832 Sodium acetylide, 1018 Sodium bromoacetylide, 0578 Sodium chloroacetylide, 0598 Sodium ethoxyacetylide, 1474 Sodium methoxyacetylide, 1120 Sodium phenylacetylide, 2906 Strontium acetylide, 1022 Tetraethynylgermanium, 2890 Tetraethynyltin, 2896 Thallium iodacetylide, 0980... 

Propynylmercapto)propane [67465-99-0] 2-Propynyl 3,7,1 l-trimethyl-2(, 4( -dodecadienoate [37882-31-8] 2-Propynyl vinyl sulphide Silver acetylide [7659-31-6] Sodium ethoxyacetylide Sodium phenylacetylide [1004-22-4] Tetraethynylgermanium [4531-35-5] Tetraethynyltin [16413-88-0] UE 4528000... 

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