Natural bond orbital (NBO) analysis is one of many available options for ‘translating’ computational solutions of Schrödinger’s wave equation into the familiar language of chemical bonding concepts. In this Review, we first address the title questions by describing characteristic features that distinguish NBO from alternative analysis methodologies (e.g. of QTAIM or EDA type) and answering criticisms that have been raised in specific chemical applications. We then address the general ‘usefulness’ of NBO analysis in the context of widely accepted philosophical criteria, including (i) broad consistency, both internally and with respect to known experimental data, (ii) multi-faceted predictive capacity, including numerical model predictions of specific properties, general correlative and statistical regression relationships, and ‘risky’ falsifiable predictions of previously unknown chemical phenomena, and (iii) general pedagogical value, promoting organisation, unification, and orderly rationalisation of chemical knowledge. Specific chemical topics chosen for discussion include controversial H⋯H ‘bond lines’ in bay-type hydrocarbon species; carbene ligation of coinage metals; resonance-type bonding of noble gas hydrides; NBO descriptors in Hammett-type quantitative structure-activity relationships; nature of conventional and ‘anti-electrostatic’ hydrogen bonding interactions; multi-centre bonding in ‘aromatic’ , Lewis-like hybridisation picture of non-VSEPR geometry and high-order multiple bonding in transition metal species; resonance origin of the ‘18e rule’; and localised (symmetry-independent) prediction of Jahn–Teller effects in free radical chemistry. We conclude with hints of some directions for future extensions of NBO methods.

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什么是 NBO 分析，它有何用处？

自然键轨道 (NBO) 分析是将薛定谔波动方程的计算解“转换”为化学键概念的熟悉语言的众多可用选项之一。在这篇评论中，我们首先通过描述区分 NBO 与替代分析方法（例如 QTAIM 或 EDA 类型）的特征并回答在特定化学应用中提出的批评来解决标题问题。然后，我们在广泛接受的哲学标准的背景下讨论 NBO 分析的一般“有用性”，包括 (i) 内部和已知实验数据方面的广泛一致性，(ii) 多方面的预测能力，包括数值模型预测特定属性，一般相关和统计回归关系，以及对先前未知的化学现象的“有风险的”可证伪预测，以及 (iii) 一般教学价值，促进化学知识的组织、统一和有序合理化。选择讨论的特定化学主题包括海湾型碳氢化合物物种中存在争议的 H⋯H“键合线”；硬币金属的卡宾连接；惰性气体氢化物的共振型键合；哈米特型定量构效关系中的 NBO 描述符；常规和“抗静电”氢键相互作用的性质；“芳香”中的多中心键合，非 VSEPR 几何结构的类路易斯杂交图片和过渡金属物种中的高阶多重键合；“18e 法则”的共振起源；自由基化学中 Jahn-Teller 效应的局部（与对称性无关）预测。