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Speciation of the lonizable Antibiotic Sulfamethazine on Black Carbon (Biochar)

机译：炭黑上可离子化的抗生素磺胺二甲嘧啶的形态（生物炭）

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摘要

Adsorption of ionizable compounds by black carbon is poorly characterized. Adsorption of the veterinary antibiotic sulfamethazine (SMT; a.k.a., sulfadimidine; pK_(a1) = 2.28, pK_(a2) = 7.42) on a charcoal was determined as a function of concentration, pH, inorganic ions, and organic ions and molecules. SMT displayed unconventional adsorption behavior. Despite its hydrophilic nature (log K_(ow) - 0.27), the distribution ratio K_d at pH 5, where SM'T~0 prevails, was as high as 10~6 L kg~(-1), up to 104 times greater than literature reported Kw. The K^ decreases at high and low pH but not commensurate with the decline in K_(ow) of the ionized forms. At pH 1, where SMT~+ is predominant and the surface is positive, a major driving force is π-π electron donor-acceptor interaction of the protonated aniline ring with the π-electron rich graphene surface, referred to as π~+-π EDA, rather than ordinary electrostatic cation exchange. In the alkaline region, where SMT~- prevails and the surface is negative, adsorption is accompanied by near-stoichiometric proton exchange with water, leading to the release of OH~- and formation of an exceptionally strong H-bond between SMT~0 and a surface carboxylate or phenolate, classified as a negative charge-assisted H-bond, (-)CAHB. At pH 5, SMT~0 adsorption is accompanied by partial proton release and is competitive with tnmethylphenylammonium ion, signifying contributions from SMT~± and/or the zwitterion, SMT~±, which take advantage of π~+-π EDA interaction and Coulombic attraction to deprotonated surface groups. In essence, both pK_(a1) and pK_(a2) increase, and SMT± is stabilized, in the adsorbed relative to the dissolved state.
机译：黑碳对可电离化合物的吸附特性不佳。确定了兽用抗生素磺胺二甲嘧啶（SMT;又名磺胺嘧啶; pK_（a1）= 2.28，pK_（a2）= 7.42）在木炭上的吸附量是浓度，pH，无机离子以及有机离子和分子的函数。 SMT表现出非常规的吸附行为。尽管具有亲水性（log K_（ow）-0.27），但在pH 5时（SM'T〜0占优势）的分布比K_d高达10〜6 L kg〜（-1），比原来大104倍比文献报道的千瓦。在高pH和低pH下K ^降低，但与电离形式的K_（ow）降低不相称。在pH值为1的情况下，SMT〜+占优势，表面为正，主要驱动力是质子化苯胺环与π电子富集的石墨烯表面的π-π电子供体-受体相互作用，称为π〜+- πEDA，而不是普通的静电阳离子交换。在SMT〜-占优势且表面为负的碱性区域，吸附伴随着接近化学计量的质子与水交换，从而导致OH〜-的释放以及SMT〜0与SMT〜0之间形成异常强的H键。表面羧酸盐或酚盐，分类为负电荷辅助H键（-）CAHB。在pH 5时，SMT〜0吸附伴随部分质子释放，并与叔甲基苯基铵离子竞争，这表明SMT〜±和/或两性离子SMT〜±的贡献，它们利用π〜+-πEDA相互作用和库仑吸引去质子化的表面基团。本质上，相对于溶解状态，pK_（a1）和pK_（a2）均增加，并且SMT±稳定。

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  • 来源
    《Environmental Science & Technology》 |2011年第23期|p.10020-10027|共8页
  • 作者

    Marc Tebrido; Joseph J. Pignatello; Jose L. Beltran; Merce Granados; Jordan Peccia;

  • 作者单位

    Departament de Quimica Analitica, Universitat de Barcelona, Marti i Franques 1-11, 08028 Barcelona, Spain;

    Department of Environmental Sciences, Connecticut Agricultural Experiment Station, New Haven, Connecticut 06504, United States,Department of Chemical and Environmental Engineering, Yale University, New Haven, Connecticut 06520, United States;

    Departament de Quimica Analitica, Universitat de Barcelona, Marti i Franques 1-11, 08028 Barcelona, Spain;

    Departament de Quimica Analitica, Universitat de Barcelona, Marti i Franques 1-11, 08028 Barcelona, Spain;

    Department of Chemical and Environmental Engineering, Yale University, New Haven, Connecticut 06520, United States;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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