Refinement of the crystal structure of triphenyl phosphate

Svetich, G. W.; Caughlan, Charles N.

doi:10.1107/s0365110x65004024

Cited by 28 publications

(5 citation statements)

References 5 publications

(4 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The P-N length in the zwitterion is 1.77 A, the single-bond length. A similar change in bond order can be observed in comparing the triester (PhO)3PO (Svetich & Caughlan, 1965) with the mono-ester mono-anion, PhO(OH)PO 2 (Kennard, Watson, Fawcett, Kerr & Coppola, 1967). In the triester, the phosphoryl bond length is 1.432 A (bond valence, 1.56) and the average length of the three P-O(ester) bonds is 1.567 A corresponding to a bond valence of 1.16.…”

Section: Bond Distances (A) and Bond Angles (O) For The Heavy Atomssupporting

confidence: 54%

The crystal and molecular structure of 2-diethylphosphorylguanidine–hemi(guanidinium chloride)

Kennard¹,

Coppola²,

Wampler³

et al. 1979

Acta Crystallogr Sect B

View full text Add to dashboard Cite

show abstract

Section: Bond Distances (A) and Bond Angles (O) For The Heavy Atomssupporting

confidence: 54%

The crystal and molecular structure of 2-diethylphosphorylguanidine–hemi(guanidinium chloride)

Kennard¹,

Coppola²,

Wampler³

et al. 1979

Acta Crystallogr Sect B

View full text Add to dashboard Cite

show abstract

“…By cornparison, the corresponding O(C)-P-O(C) bond angle in a six-membered cyclic phosphate system, namely the nucleotide uridine 3', 5'-monophosphate (Coulter, 1969), was found to be 103.1 ° (average of two values). In acyclic systems, O(C)-P-O(C) bond angles are in general very close to this value, as can be seen for trisp-nitrophenyl phosphate, 103.1 ° (average of three angles) (Mazhar-ul-Haque & Caughlan, 1970); bis-pnitrophenyl phosphate (procaine complex), 103.3 ° (Sax, Pletcher & Gustaffson, 1970); dibenzylphosphoric acid, 103.8 ° (Dunitz & Rollett, 1956); L-c~-glycerylphosphorylcholin, 103.1 ° (Abrahamsson & Pascher, 1966); and triphenyl phosphate, 101.5 ° (average of two values) (Svetich & Caughlan, 1965). The value of 108.1 o reported for bis-p-chlorophenyl phosphate (Calleri & Speakman, 1964) appears to be above the normal range.…”

Section: Discussionmentioning

confidence: 99%

The crystal and molecular structure of catechol cyclic phosphate

Boer¹

1972

Acta Crystallogr Sect B

View full text Add to dashboard Cite

1201h6t6rocycle glucidique 5-cinq cha~nons. Ce compos6 pr6sente le double int6r& d'etre 5-la fois un pr6curseur extrfimement utile 5. la synth6se d'analogues des nucl6-osides glucofuranosidiques et de pr6senter une conformation du cycle tout 5-fait originale.Les auteurs remercient M. J. Defaye de leur avoir fourni le sujet de ce travail. The crystal structure of catechol cyclic phosphate, C6HsPO4, has been determined from three-dimensional X-ray diffraction data. The orthorhombic unit cell, space group Pbca (D~) has lattice parameters a= 8.549 (2), b= 15.041 (3), and c= 11.053 (2) A, giving a calculated density of 1.608 g.cm -a for M.W. 172"078 and Z= 8. The intensities of 1211 unique reflections were measured using the 0-20 scan mode of a Picker automatic 4-circle diffractometer and Cu Kct radiation. The structure was solved from the Patterson function, and the positions and anisotropic temperature factors of the P, O, and C atoms were refined by full-matrix least-squares methods. Hydrogen atoms were located, and in some cases refined. The final R values were R1=0"063 and R2=0"052 for the 851 reflections above background. The ring system is essentially planar. The O-P-O bond angle in the highly strained five-membered ring is 98-4+ 0"2 °. Some distortion occurs in the six-membered ring as indicated by bond angles of 115.2 and 115.9 ° at the ~-carbon atoms. The crystal structure contains infinite hydrogen bonded chains, proceeding in the x direction and generated by the a glide, linking the phosphoryl and hydroxyl oxygen atoms of adjacent molecules with an O-H.-. O distance of 2.464 A. R6f6rences

show abstract

“…The distances 1.471 and 1.480 ,~ found in the phosphoenolpyruvate ion are probably not significantly different from the values 1.496 and 1.513/~ in the HzPO~ ion of the hydrolysed cocarboxylase structure and some of the values listed in Table 4. For the diester, dibenzylphosphoric acid (Dunitz & Rollett, 1956), the P=O distance is 1.469 A but for the triesters, methyl ethylene phosphate (Steitz & Lipscomb, 1965), triphenyl phosphate (Svetich & Caughlan, 1965), and tri-p-nitrophenyl phosphate (Mazhar-ul-Haque & Caughlan, 1970), the values are 1.44, 1.43 and 1.44 A respectively. Thus in the case of the triesters the P=O bond appears to be more nearly a 'pure' double bond with a smaller contribution fiom the charged species.…”

Section: Molecular Dimensionsmentioning

confidence: 99%