scholarly journals Comparison of zwitterionic N-alkylaminomethanesulfonic acids to related compounds in the Good buffer series

2010 ◽  
Vol 6 ◽  
Author(s):  
Robert D Long ◽  
Newton P Hilliard ◽  
Suneel A Chhatre ◽  
Tatiana V Timofeeva ◽  
Andrey A Yakovenko ◽  
...  
Keyword(s):  
Sulfonic Acid ◽  
Aqueous Solubility ◽  
Carbon Chain ◽  
Secondary Amines ◽  
Ammonium Ion ◽  
X Ray ◽  
Crystallographic Structures ◽  
Related Compounds ◽  
Sulfonic Acid Groups ◽  
Biological Buffers

Several N-alkyl and N,N-dialkylaminomethanesulfonic acids were synthesized (as zwitterions and/or sodium salts) to be tested for utility as biological buffers at lower pH levels than existing Good buffer compounds (aminoalkanesulfonates with a minimum of two carbons between amine and sulfonic acid groups as originally described by Norman Good, and in common use as biological buffers). Our hypothesis was that a shorter carbon chain (one carbon) between the amino and sulfonic acid groups should lower the ammonium ion pK a values. The alkylaminomethanesulfonate compounds were synthesized in aqueous solution by reaction of primary or secondary amines with formaldehyde/sodium hydrogensulfite addition compound. The pK a values of the ammonium ions of this series of compounds (compared to existing Good buffers) was found to correlate well with the length of the carbon chain between the amino and sulfonate moeties, with a significant decrease in amine basicity in the aminomethanesulfonate compounds (pK a decrease of 2 units or more compared to existing Good buffers). An exception was found for the 2-hydroxypiperazine series which shows only a small pK a decrease, probably due to the site of protonation in this compound (as confirmed by X-ray crystal structure). X-ray crystallographic structures of two members of the series are reported. Several of these compounds have pK a values that would indicate potential utility for buffering at pH levels below the normal physiological range (pK a values in the range of 3 to 6 without aqueous solubility problems) – a range that is problematic for currently available Good buffers. Unfortunately, the alkylaminomethanesulfonates were found to degrade (with loss of their buffering ability) at pH levels below the pK a value and were unstable at elevated temperature (as when autoclaving) – thus limiting their utility.

The Pyrolytic Rearrangement of 1-Alkynoyl-3-methylpyrazoles: Synthesis of Pyrazolo[1,5-a]pyridin-5-ols and Related Compounds

1994 ◽  
Vol 47 (6) ◽  
pp. 991 ◽  
Author(s):  
RFC Brown ◽  
FW Eastwood ◽  
GD Fallon ◽  
SC Lee ◽  
RP Mcgeary
Keyword(s):  
Carbon Chain ◽  
Ring Structure ◽  
High Yield ◽  
Methyl Group ◽  
X Ray ◽  
X Ray Crystallography ◽  
Flash Vacuum Pyrolysis ◽  
Vacuum Pyrolysis ◽  
Fused Ring ◽  
Related Compounds

Flash vacuum pyrolysis of 1-(alkyn-2′-oyl)-3-methylpyrazoles at 650°/0.03 mm forms pyrazolo[1,5-a]pyridin-5-ols, often in high yield, which may bear substituents at C2, C3 or C7. In the absence of a 3-methyl group in the precursor, N-ethynylpyrazoles are formed in low yield. The formation of both types of product is interpreted as involving 3-(N-pyrazolyl)propadienones formed by N1 → N2 migration of the N-alkynoyl group with inversion of the three-carbon chain. The fused-ring structure of 2-methylpyrazolo[1,5-a]pyridin-5-ol (25) was established by X-ray crystallography of the O-benzoyl derivative (27).

scholarly journals Synthesis of Sulfonic Acid-Functionalized Zirconium Poly(Styrene-Phenylvinyl-Phosphonate)-Phosphate for Heterogeneous Epoxidation of Soybean Oil

Catalysts ◽  
2019 ◽  
Vol 9 (9) ◽  
pp. 710 ◽  
Author(s):  
Xiaochuan Zou ◽  
Xuyuan Nie ◽  
Zhiwen Tan ◽  
Kaiyun Shi ◽  
Cun Wang ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Soybean Oil ◽  
Sulfonic Acid ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Thiol Group ◽  
Catalytic Performance ◽  
X Ray ◽  
Sulfonic Acid Groups

In this paper, a solid acid catalyst (ZPS–PVPA–SO3H) was prepared by anchoring thiol group on zirconium poly(styrene-phenylvinyl-phosphonate)-phosphate (ZPS–PVPA), followed by oxidation of thiol groups to obtain sulfonic acid groups. The solid acid catalyst was characterized by XPS, X-ray, EDS, SEM, and TG-DSC. The successful preparation of sulfonic acid-functionalized ZPS–PVPA was confirmed. Subsequently, the catalytic performance of ZPS–PVPA–SO3H was investigated in the epoxidation of soybean oil. The results demonstrated that ZPS–PVPA–SO3H can effectively catalyze epoxidation of soybean oil with TBHP as an oxidant. Moreover, there was no significant decrease in catalytic activity after 5 repeated uses of the ZPS–PVPA–SO3H. Interestingly, the ZPS–PVPA–SO3H was kept in 2 mol/L of HCl overnight after the end of the seventh reaction, and the catalytic activity was gradually restored during the eighth to tenth cycles.

Mild surface modification of para-aramid fiber by dilute sulfuric acid under microwave irradiation

2016 ◽  
Vol 87 (7) ◽  
pp. 799-806 ◽  
Author(s):  
Tingting Deng ◽  
Guangxian Zhang ◽  
Fangyin Dai ◽  
Fengxiu Zhang
Keyword(s):  
Surface Modification ◽  
Sulfuric Acid ◽  
Microwave Irradiation ◽  
Sulfonic Acid ◽  
Breaking Strength ◽  
Aramid Fiber ◽  
Aramid Fibers ◽  
X Ray ◽  
Dilute Sulfuric Acid ◽  
Sulfonic Acid Groups

In aramid fiber-reinforced composites manufacturing, para-aramid fiber requires surface modification to improve its interfacial adhesion with matrix materials. In this study, aramid fiber was modified with dilute sulfuric acid, which was gradually concentrated under microwave irradiation. Results showed that the aramid fiber could be efficiently modified. Sulfonic acid groups were introduced on the surface of the aramid fiber, as confirmed by X-ray photoelectron spectroscopy and Fourier transform infrared spectroscopy. The breaking strength and thermal stability of the modified aramid fiber were not adversely affected. When the concentration of sulfuric acid was 30.0 g/L, the breaking strength of the aramid fiber remained at 90.7% of the original value, and the number of sulfonic acid groups of 1 g modified aramid fibers was 1.38 × 10–5 mol/g. Thermogravimetric and X-ray diffraction analyses showed that the main structure of the aramid fibers was not affected. The aramid fiber surface was not severely etched, as evidenced by scanning electron microscopy images. Therefore, this modifying method involving a gradual change in sulfuric acid concentration may be widely applied in many fields.

scholarly journals Crystal Chemical Relations in the Shchurovskyite Family: Synthesis and Crystal Structures of K2Cu[Cu3O]2(PO4)4 and K2.35Cu0.825[Cu3O]2(PO4)4

Crystals ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 807
Author(s):  
Ilya V. Kornyakov ◽  
Sergey V. Krivovichev
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Structural Complexity ◽  
Crystal Chemical ◽  
X Ray Diffraction ◽  
Complexity Measures ◽  
X Ray ◽  
The Family ◽  
Similarities And Differences ◽  
Related Compounds

Single crystals of two novel shchurovskyite-related compounds, K2Cu[Cu3O]2(PO4)4 (1) and K2.35Cu0.825[Cu3O]2(PO4)4 (2), were synthesized by crystallization from gaseous phase and structurally characterized using single-crystal X-ray diffraction analysis. The crystal structures of both compounds are based upon similar Cu-based layers, formed by rods of the [O2Cu6] dimers of oxocentered (OCu4) tetrahedra. The topologies of the layers show both similarities and differences from the shchurovskyite-type layers. The layers are connected in different fashions via additional Cu atoms located in the interlayer, in contrast to shchurovskyite, where the layers are linked by Ca2+ cations. The structures of the shchurovskyite family are characterized using information-based structural complexity measures, which demonstrate that the crystal structure of 1 is the simplest one, whereas that of 2 is the most complex in the family.

scholarly journals Stereoselective Convergent Synthesis of Carbon Skeleton of Cotylenin A Aglycone

Synthesis ◽  
2021 ◽  
Author(s):  
Kazuyuki Sugita ◽  
Motoi Kuwabara ◽  
Ami Matsuo ◽  
Shogo Kamo ◽  
Akinobu Matsuzawa
Keyword(s):  
Single Crystal ◽  
Aldol Reaction ◽  
Coupling Reaction ◽  
Carbon Skeleton ◽  
Convergent Synthesis ◽  
X Ray ◽  
Related Compounds

AbstractIn this paper, the synthesis of the carbon skeleton of cotylenin A aglycone is described. The key reactions, including an intramolecular aldol reaction, an aldol coupling reaction, and a ring-closing meta­thesis, allow for the effective and stereoselective access to the carbon skeleton of cotylenin A aglycone. The stereochemistry was confirmed by single-crystal X-ray crystallographic analyses of related compounds.

The preparation of sodium 4-Amino-3-nitro-benzenesulfonate and some related compounds

1982 ◽  
Vol 35 (8) ◽  
pp. 1727 ◽  
Author(s):  
J Rosevear ◽  
JFK Wilshire
Keyword(s):  
Sodium Hydroxide ◽  
Nitro Group ◽  
Sodium Salt ◽  
Sulfonic Acid ◽  
Sodium Hydroxide Solution ◽  
Hydroxide Solution ◽  
Dilute Sodium Hydroxide ◽  
Related Compounds

The sodium salt of 4-amino-3-nitrobenzenesulfonic acid (O-nitroaniline-p-sulfonic acid) has been prepared by the action of dilute sodium hydroxide solution on ethyl [(4-chlorosulfonyl-2-nitro)- phenyllcarbamate. Central to this synthesis is the finding that the N-ethoxycarbonyl group, when located ortho to a nitro group (but not to a bromo group), is readily removed by dilute sodium hydroxide solution.

scholarly journals Methoxylation of α-pinene over poly(vinyl alcohol) containing sulfonic acid groups

2009 ◽  
Vol 147 (2-3) ◽  
pp. 302-306 ◽  
Author(s):  
D.S. Pito ◽  
I.M. Fonseca ◽  
A.M. Ramos ◽  
J. Vital ◽  
J.E. Castanheiro
Keyword(s):  
Vinyl Alcohol ◽  
Sulfonic Acid ◽  
Poly Vinyl Alcohol ◽  
Sulfonic Acid Groups
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