2,7-Disubstituted proton sponges as borderline systems for investigating barrier-free intramolecular hydrogen bonds. Protonated 2,7-bis(trimethylsilyl)- and 2,7-di(hydroxymethyl)-1,8-bis(dimethylamino)naphthalenes

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6209-6214

  Degtyarev, Alexander V ^a   Ryabtsova, Oxana V ^a   Pozharskii, Alexander F ^a   Ozeryanskii, Valery A ^a   Starikova, Zoya A ^b   Sobczyk, Lucjan ^c   Filarowski, Alexander ^c  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c UNIVERSITY OF WROC AW   (Poland)

Author keywords

Intramolecular hydrogen bond; Molecular structure; Proton transfer; Sterically modified proton sponges

Indexed keywords

2,7 BIS(TRIMETHYLSILYL) 1,8 BIS(DIMETHYLAMINO)NAPHTHALENE; 2,7 DI(HYDROPXYMETHYL) 1,8 BIS(DIMETHYLAMINO)NAPHTHALENE; HYDROGEN; NAPHTHALENE DERIVATIVE;

ARTICLE; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON TRANSPORT; ROOM TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 44349166817     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.001     Document Type: Article

References (30)

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19. -] the R-factor is rather low, the NH proton is not localized, while in the anionic part [H(O-B) atoms] three protons are localized even including the disordered proton. Furthermore, there are some doubts on geometry of the naphthalene fragment: the C9-N2 bond (1.447 Å) is unbelievably shorter than the C1-N1 1.482 Å; the C1-C2 bond is also unusually short (1.332 Å). Hence, the sharpness and correctness of the MUQMUG structure is questionable and this entry has to be done at low temperature.
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27. + bridge in 6 can be attributed to insufficiently precise DFT theoretical methods when they are applied to very strong hydrogen bonds. The results obtained in Ref. 28 should be interpreted that the length 2.578 Å is theoretically overestimated and there should be taken into account an effect of the packing.
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29. + distance reaches 2.760 Å and the NHN angle is as sharp as 142° (the record value among all known proton sponge salts). The situation seems to look as if the counter-ion has already essentially extracted the NH proton from its cavity
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